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

HRID 75318Notes

Reaction equation

HRID 75318 reaction equation
[CH3:1][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]([CH3:1])[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

4

Reactant 2

HCID 222AmmoniaHCID 86707982(S)-4-Methyl-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile

Product 1

HCID 72709649(S)-2-Amino-4-methyl-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(S)-4-Methyl-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (15 mg, 0.033 mmol) in dioxane (2 mL) was combined with ammonia in dioxane 0.5 M (0.198 mL, 0.099 mmol) to give a yellow solution, which was stirred for 6 hours at room temperature. The product was purified by LC/MS using a 20-45% 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 (2 mg, 17%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.47 (m, 3 H), 2.17-2.28 (m, 3 H), 2.70-2.85 (m, 2 H), 2.96-3.13 (m, 2 H), 3.67-3.92 (m, 8 H), 5.82-5.97 (m, 1 H), 6.45-6.59 (m, 1 H), 6.87-6.98 (m, 2 H), 7.52-7.62 (m, 1 H), 7.82-7.91 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C20H24N8O3S, 393.4; found 393.4.

Workup

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

Sources & evidence

ORD record
ord-9e19731e21434e25a5ec7a99fb31efb1
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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