Ammonia → (S)-2,4-diamino-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrile

HRID 75319Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH3:12])[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[NH3:33]>O1CCOCC1>[NH2:33][C:4]1[N:3]=[C:2]([NH2:1])[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH3:12])[N:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(S)-4-Amino-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (108 mg, 0.237 mmol) in dioxane (3 mL) was combined with 0.5 M ammonia in dioxane (1.419 mL, 0.710 mmol) to give a yellow solution, which was stirred overnight at 60° C. The product was purified by LC/MS using a 5-30% CH3CN gradient in H2O with 0.035% formic acid. The pure fractions were combined and lyophilized to give a formic acid salt of the title compound as a white solid (14 mg, 15%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43-1.59 (m, 3 H), 2.74-2.87 (m, 2 H), 3.03-3.17 (m, 2 H), 3.70-3.99 (m, 8 H), 5.76-5.91 (m, 1 H), 6.52-6.69 (m, 1H), 7.45-7.48 (br s, 2 H), 7.52-7.62 (m, 1 H), 7.75-7.79 (br s, 2 H), 7.82-7.91 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C19H23N9O, 394.4; found 394.5.

Workup

customto give a yellow solution, which
customThe product was purified by LC/MS

Sources & evidence

ORD record: ord-6dbbfa22c488438d9bda35b444dc2d98
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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