Supporting Information-B. A Facile Iterative Synthesis of 2,5-Terpyrimidinylenes as Non-peptidic α-helical Mimics

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Supporting Information-B A Facile Iterative Synthesis of 2,5-Terpyrimidinylenes as on-peptidic α-helical Mimics Laura Anderson, 1,2 Mingzhou Zhou, 1,2 Vasudha Sharma, 2 Jillian M. McLaughlin, 2 Daniel. Santiago, 1 Frank R. Fronczek, 3 Wayne C. Guida, 1,2 and Mark L. McLaughlin 1,2, * 1 Department of Chemistry, University of South Florida, 422 E. Fowler Ave, Tampa, Florida 3362, 2 Department of Drug Discovery, H. Lee Moffitt Cancer Center, 1292 Magnolia Dr, Tampa, Florida 33612, and 3 Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 78 1 H & 13 C Spectra of Compounds: 2a f. S2 3a j. S8 4-1 4-13...S17 5-1 5-7. S31 6-1 6-5..S39 S1

5-Methyl-3-oxohexanenitrile (2a) C 2.6 2.5 2.4 2.3 2.2 2.1 2. 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 -2 C S2

3-xo-4-phenylbutanenitrile (2b) C 3.14 1.88 2.7 1.99 C S3

S4 5-Cyclohexyl-3-oxo pentanenitrile(2d) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 C C

S5 Methyl 2-(naphthalen-2-yl)acetate -4-3 -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 Me Me

4-(aphthalen-1-yl)-3-oxobutanenitrile (2e) C 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 -2-3 -4 C S6

4-(aphthalen-2-yl)-3-oxobutanenitrile (2f) C C 22 21 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 S7

(E/Z)-2-((Dimethylamino)methylene)-5-methyl-3-oxohexanenitrile (3a) C.76 2.72 2.77 2.2 1.12 6. C S8

(E/Z)-2-((Dimethylamino)methylene)-3-oxo-4-phenylbutanenitrile (3b) C C S9

(E/Z)-2-((Dimethylamino)methylene)-4-methyl-3-oxopentanenitrile (3c) C C S1

S11 (E/Z)-5-Cyclohexyl-2-((dimethylamino)methylene)-3-oxopentanenitrile (3d) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 C Me 2 C Me 2

(E/Z)-2-((Dimethylamino)methylene)-4-(naphthalen-1-yl)-3-oxobutanenitrile (3e) C.97 1.93.94 3.9 2.14 3. 3.14 C S12

(E/Z)-2-((Dimethylamino)methylene)-4-(naphthalen-2-yl)-3-oxobutanenitrile (3f) C C S13

(E/Z)-2-((Dimethylamino)methylene)-3-oxobutanenitrile (3g) C Me 2 C Me 2 225 2 175 15 125 1 75 5 25 S14

(E/Z)-2-((Dimethylamino)methylene)-4,4-dimethyl-3-oxopentanenitrile (3i) C C S15

(E/Z)-2-Benzoyl-3-(dimethylamino)acrylonitrile (3j) C C S16

2-Amino-4-benzylpyrimidine-5-carbonitrile (4-1) H 2 C H 2 C S17

4-Benzylpyrimidine-5-carbonitrile (4-2) C.81.82 4.91 2.1 4.84 C S18

4-Benzyl-2-methylpyrimidine-5-carbonitrile (4-3) C.82 5.18 2.24 2.99 C S19

4-Benzyl-2-phenylpyrimidine-5-carbonitrile (4-4) C C S2

S21 4-Isobutyl-2-phenylpyrimidine-5-carbonitrile (4-5) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 6.46 1. 2.24 3.4 1.92.79 7.5 7.7 7.9 8.1 8.3 8.5 8.7 3.4 1.92 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 2.9 3. 3.1 1. 2.24 C C

2-Amino-4-isobutylpyrimidine-5-carbonitrile (4-6) H 2 C.73 1.83 2.3 1. 5.88 2.3.99 H 2 C 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1 S22

S23 4-Isopropyl-2-methylpyrimidine-5-carbonitrile (4-7) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 C C

4-Isopropyl-2-phenylpyrimidine-5-carbonitrile (4-8) C C S24

2-Amino-4-isopropylpyrimidine-5-carbonitrile (4-9) H 2 C H 2 C S25

4-(2-Cyclohexylethyl)-2-methylpyrimidine-5-carbonitrile (4-1) C.82 2.14 3. 7.91 5.53 1.82 C 22 21 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 S26

4-(2-Cyclohexylethyl)-2-phenylpyrimidine-5-carbonitrile (4-11) C 13 12 11 1 9 8 7 6 5 4 3 2 1-1 -2 C S27

4-tert-Butyl-2-phenylpyrimidine-5-carbonitrile (4-12) C 8.5 8.3 8.1 7.9 7.7 7.5 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 -2 C S28

2-Amino-4-tert-butylpyrimidine-5-carbonitrile (4-13) H 2 C.78 2.8 9. H 2 C S29

4,4'-Diisobutyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-1) C C S3

4-Benzyl-4'-isobutyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-2) C C 132 131 13 129 22 21 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 S31

S32 4'-Benzyl-4-(naphthalen-2-ylmethyl)-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-3) -1 1 2 3 4 5 6 7 8 9 1 11 12 13 14-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 C C

S33 4'-Benzyl-4-methyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-4) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 122 124 126 128 13 132 134 C C

2'-Amino-4-benzyl-4'-isobutyl-2,5'-bipyrimidine-5-carbonitrile (5-5) H 2 C H 2 C 22 21 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 S34

S35 4'-Benzyl-4-isobutyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-6): -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 2.1 2.2 2.3 2.4-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 15 16 17 18 19 2 21 22 125 13 C C

4'-Benzyl-4-(naphthalen-1-ylmethyl)-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-7): C 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 C S36

Crystal data C33H235 F = 124 Mr = 489.56 Dx = 1.343 Mg m 3 Monoclinic, P21/n Mo Kα radiation λ =.7173 Å Hall symbol: -P 2yn Cell parameters from 538 reflections a = 9.3452 (15) Å θ = 2.5 27.1º b = 22.46 (3) Å µ =.8 mm 1 c = 12.229 (16) Å T = 9. (5) K β = 12.148 (9)º Plate fragment,? V = 2421.5 (6) Å3.3.27.7 mm Z = 4 Data collection KappaCCD (with xford Cryostream) diffractometer 3888 reflections with I > 2σ(I) Radiation source: fine-focus sealed tube Rint =.27 Monochromator: graphite θmax = 27.1º T = 9.(5) K θmin = 2.6º ω and φ scans h = 11 11 S37

Absorption correction: none k = 28 28 39528 measured reflections l = 15 15 5294 independent reflections Refinement Refinement on F2 Secondary atom site location: difference Fourier map Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites R[F2 > 2σ(F2)] =.47 H-atom parameters constrained wr(f2) =.11 w = 1/[σ2(Fo 2) + (.427P)2 +.755P] where P = (Fo 2 + 2Fc 2)/3 S = 1.7 ( /σ)max <.1 5294 reflections ρmax =.22 e Å 3 415 parameters ρmin =.2 e Å 3 32 restraints Extinction correction: SHELXL, Fc*=kFc[1+.1xFc2λ3/sin(2θ)]-1/4 S38

5 -Cyano-4 -isopropyl-4 -phenylmethyl-4-isobutyl-2-phenylterpyrimidine (6-1) C C 22 21 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 S39

S4 5 -Cyano-4,4 -diisobutyl-4 -(2-naphthylmethyl)-2-phenylterpyrimidine (6-2) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 5.94 6.14 2.18 2.12 2.1 2. 2.94 3.28 1.8 3.27 2.14.85.89.88 7.4 7.5 7.6 7.7 7.8 2.94 3.28 1.8 3.27 2.2 2.3 2.18 C C

5 -Cyano-4,4 -diisobutyl-4 -(2-phenylmethyl)-2-phenylterpyrimidine (6-3) C 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 -2 C S41

5 -Cyano-4,4 -diisobutyl-4 -(1-naphthylmethyl)-2-phenylterpyrimidine(6-4) C C 22 21 2 19 18 17 16 15 14 13 12 11 1 9 8 7 6 5 4 3 2 1-1 S42

S43 5 -Cyano-4 -isobutyl-4 -(1-naphthylmethyl)-4-(2-phenylmethyl)-2-phenylterpyrimidine(6-5) -2-1 1 2 3 4 5 6 7 8 9 1 11 12 13 14 6.69 1.39 2.21 2. 2. 6.24 1.77 5.65 1.14 1.7 1.9 2.13.69.79.72 C C

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