Water → 6-Amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-7,9-dimethyl-7,9-dihydro-8H-purin-8-one

HRID 510091Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:29])[C:5](=[O:28])[NH:6]2.[CH3:30]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.IC.O>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:29])[C:5](=[O:28])[N:6]2[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

300 mg (0.768 mmol) of the compound from example 41 and 211 mg (0.768 mmol) of BEMP were initially charged in 10 ml of dimethylformamide, and a solution of 109 mg (0.768 mmol) of iodomethane in 2 ml of dimethylformamide was added dropwise at 0° C. within 10 min. The mixture was stirred at 0° C. for 3 h. Water was added, which formed a precipitate. The precipitate was filtered off and purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10). 203 mg of the title compound were obtained (65% of theory).

Workup

customwhich formed a precipitate
filtrationThe precipitate was filtered off
custompurified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10)

Sources & evidence

ORD record: ord-fb2fa931e08847a8948f7cc21a9fb2f6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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