Water → 4-(2-Amino-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid phenylamide

HRID 1052015Notes

Reaction equation

[O-]CC.[Na+].C(=O)(O)O.[NH2:9][C:10]([NH2:12])=[NH:11].[C:13]1([NH:19][C:20]([C:22]2[CH:27]=[C:26]([N:28]3[CH2:32][C:31](=O)[C:30](=[CH:34]N(C)C)[CH2:29]3)[CH:25]=[CH:24][N:23]=2)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C(O)C>[C:13]1([NH:19][C:20]([C:22]2[CH:27]=[C:26]([N:28]3[CH2:29][C:30]4[CH:34]=[N:9][C:10]([NH2:12])=[N:11][C:31]=4[CH2:32]3)[CH:25]=[CH:24][N:23]=2)=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of sodium ethoxide (0.18 mL, 0.56 mmol, 3M) in ethanol (10 mL) was added guanidine carbonate (50 mg, 0.56 mmol). The suspension was stirred for 45 minutes, then added to a suspension of 4-(3-((Dimethylamino)methylene)-4-oxopyrrolidin-1-yl)-pyridine-2-carboxylic acid phenylamide (95 mg, 0.28 mmol) in ethanol (10 mL). The reaction mixture was heated at 80° C. for 18 hours. Water (20 mL) was added and the mixture stirred for 1 hour. The solid was isolated by filtration and vacuum dried at 50° C. for 115 h and gave the title compound (44 mg, 0.13 mmol, 47%).

Workup

stirringthe mixture stirred for 1 hour
customThe solid was isolated by filtration and vacuum
customdried at 50° C. for 115 h

Sources & evidence

ORD record: ord-b5d20844567a4255bb5d379671d725f2
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388176B2

Reaction notes

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