Water → 5-(2-Amino-pyrimidin-4-yl)-2-(2,4-dichloro-phenyl)-1h-pyrrole-3-carbonitrile

HRID 1948837Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11]([C:16](=O)/[CH:17]=[CH:18]/N(C)C)=[CH:12][C:13]=1[C:14]#[N:15].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29].O>CN(C)C=O>[NH2:29][C:28]1[N:30]=[C:16]([C:11]2[NH:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:13]([C:14]#[N:15])[CH:12]=2)[CH:17]=[CH:18][N:27]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of 2-(2,4-dichloro-phenyl)-5-((E)-3-dimethylamino-acryloyl)-1H-pyrrole-3-carbonitrile (6.80 g, 20.35 mmol) in 82 mL of N,N-dimethylformamide was added guanidine carbonate (9.17 g, 101.75 mmol). The mixture was heated to 110° C. for 18 hours under efficient stirring. Then, a further amount of guanidine carbonate (1.83 g; 20.35 mmol) was added to the mixture and heating to 115° C. was prolonged for additional 22 hours. The resulting mixture was diluted by dropwise addition of 325 mL of water over 30 minutes. The solid was isolated by filtration, washed with 100 mL of water, dried in the air and, finally, in a vacuum oven at 60° C. affording 5.58 g of product as a light brown powder. Yield=83%.

Workup

temperatureheating to 115° C.
customThe solid was isolated by filtration
washwashed with 100 mL of water
customdried in the air

Sources & evidence

ORD record: ord-86ad13a40015422799eb249c7800c0e3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399668B2

Reaction notes

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