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

HRID 1052015
Notes
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Reaction equation

HRID 1052015 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)HCID 2723922Sodium ethoxideHCID 866958294-(3-((Dimethylamino)methylene)-4-oxopyrrolidin-1-yl)-pyridine-2-carboxylic acid phenylamide

Product 1

HCID 866958304-(2-Amino-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid phenylamideYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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

  1. stirringthe mixture stirred for 1 hour
  2. customThe solid was isolated by filtration and vacuum
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes