Dimethylformamide → Ethyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate

HRID 346538Notes

Reaction equation

[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1.[CH3:32]N(C=O)C.[H-].[Na+].IC>O>[NH2:1][C:2]1[C:7]([N:8]([CH3:32])[C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

54 mg (0.13 mmol) of ethyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylcarbamate from Example 2 are added to 5 ml of DMF, the mixture is cooled to 0° C., and 7.67 mg (0.19 mmol) of sodium hydride are added. Then 18.14 mg (0.13 mmol) of iodomethane are added dropwise, and the mixture is stirred for one hour. The mixture is mixed with water and extracted with dichloromethane. The combined organic phases are dried over magnesium sulphate and concentrated in a rotary evaporator. The residue is purified first by column chromatography (mobile phase: dichloromethane/methanol=10:1) and then by preparative RP-HPLC.

Workup

extractionextracted with dichloromethane
dry with materialThe combined organic phases are dried over magnesium sulphate
concentrationconcentrated in a rotary evaporator
customThe residue is purified first by column chromatography (mobile phase: dichloromethane/methanol=10:1)

Sources & evidence

ORD record: ord-36c8872da63a4eb69d53207af522fe06
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173037B2

Reaction notes

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