Aminoammonium hydroxide → 4-(3-aminopropyl)-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-ylamine

HRID 1035479Notes

Reaction equation

[OH-].[NH3+]N.[NH2:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[C:7]([C:25]2[C:33]3[C:28](=[N:29][CH:30]=[C:31]([C:34]4[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=4)[CH:32]=3)[NH:27][CH:26]=2)[N:6]=1>CO>[NH2:14][CH2:13][CH2:12][CH2:11][C:9]1[CH:8]=[C:7]([C:25]2[C:33]3[C:28](=[N:29][CH:30]=[C:31]([C:34]4[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=4)[CH:32]=3)[NH:27][CH:26]=2)[N:6]=[C:5]([NH2:4])[N:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

8.6 0.003 ml (0.06 mmol) of hydrazinium hydroxide is added at RT to a solution of 29 mg (0.06 mmol) of 2-(3-{2-amino-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-4-yl]propyl)isoindole-1,3-dione in 0.5 ml of methanol. The reaction solution is heated for 5 min at 60° C. in the microwave. The reaction mixture is evaporated in vacuo, and the residue is purified by preparative HPLC, giving 4-(3-aminopropyl)-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-ylamine as yellow solid, ESI 349

Workup

customThe reaction mixture is evaporated in vacuo
customthe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-3a98608fc24e41e994e882847fe3373c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546390B2

Reaction notes

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