Diisopropylethylamine → HCID 178422039, compound

HRID 409032Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[CH3:11][C:12]1[S:29][C:15]2=[N:16][C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:18]([C@@H:20]([NH2:22])[CH3:21])[CH:19]=[C:14]2[CH:13]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:11][C:12]1[S:29][C:15]2=[N:16][C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:18]([C@@H:20]([NH:22][C:2]3[N:10]=[CH:9][N:8]=[C:7]4[C:3]=3[N:4]=[CH:5][NH:6]4)[CH3:21])[CH:19]=[C:14]2[CH:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6-Chloropurine (26.4 mg, 0.171 mmol), (S)-1-(2-methyl-6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethanamine (40 mg, 0.148 mmol) and hunig's base (38.9 μL, 0.223 mmol) was dissolved in 2 mL of n-butanol and heated to 120° C. overnight. The reaction was cooled to rt and purified by reverse phase chromatography to afford (S)—N-(1-(2-methyl-6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethyl)-9H-purin-6-amine. 1H NMR (400 MHz, CDCl3) δ 12.5 (br s, 1H), 8.78 (br m, 1H), 8.55-7.80 (series of m, 6H), 7.60-7.30 (br m, 1H), 7.26 (m, 1H), 6.89 (br s, 1H), 6.40-6.00 (br m, 1H), 2.60 (br s, 3H), 1.60-1.25 (series of M, 3H). LC/MS (M+1, found=388.1).

Workup

temperatureThe reaction was cooled to rt
custompurified by reverse phase chromatography

Sources & evidence

ORD record: ord-773997c5fbbb4c5087dc4f2162d57348
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759371B2

Reaction notes

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