Sodium Carbonate → HCID 11741951, compound

HRID 720259Notes

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[N:15]=[C:14]([NH2:16])[C:13]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[CH:12][N:11]=2)=[N:2]1.C(=O)([O-])[O-].[Na+].[Na+].[C:29]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br)#[N:30]>CN(C)C=O>[NH2:16][C:14]1[C:13]([C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)=[CH:12][N:11]=[C:10]([C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:1]([CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[C:29]#[N:30])[N:2]=2)[N:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

60 mg (0.21 mmol) of 2-(1H-pyrazolo[3,4-b]pyridin-3-yl)-5-(4-pyridinyl)-4-pyrimidinylamine from Example 35 A are suspended in 6 ml of dimethylformamide under argon. Addition of 26.38 mg (0.25 mmol) of sodium carbonate is followed by stirring at 50° C. for one hour. Then 40.66 mg (0.21 mmol) of 2-cyanobenzyl bromide are added thereto, and the mixture is stirred at 50° C. overnight. For work up, the mixture is filtered and the filtrate is adjusted to pH 4–5 with 1 normal hydrochloric acid and purified by preparative RP-HPLC.

Workup

stirringthe mixture is stirred at 50° C. overnight
filtrationFor work up, the mixture is filtered
custompurified by preparative RP-HPLC

Sources & evidence

ORD record: ord-3505fb112ee34bb584008100ef9958a3
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135474B2

Reaction notes

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