Triethylamine → Ethyl 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-8-oxo-8,9-dihydro-7H-purine-6-carboxylate

HRID 510122Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:4][C:5]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:10]=2)=[N:6][C:7]=1[NH2:8].C1N=CN([C:36](N2C=NC=C2)=[O:37])C=1.C(N(CC)CC)C>CN(C)C=O.O.C(OCC)(=O)C>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:11]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[C:9]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:36](=[O:37])[NH:8]3)=[C:3]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:4]=2)=[N:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

225 mg (0.55 mmol) of the compound from example 63A were initially charged in dimethylformamide (2.5 ml), then 448 mg (2.76 mmol) of N,N-carbonyldiimidazole and 0.96 ml (6.90 mmol) of triethylamine were added and the mixture was stirred at 100° C. overnight. The reaction mixture was subsequently diluted with water and ethyl acetate, and filtered. The solids were washed with water and, after drying under high vacuum, gave 112 mg (46% of theory) of the title compound.

Workup

filtrationfiltered
washThe solids were washed with water
customafter drying under high vacuum

Sources & evidence

ORD record: ord-b5fee0b64f2f40a4ad7f26a3d77db0c0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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