Hydrochloric Acid → Methyl 2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}-pyrimidine-4-carboxylate

HRID 16450Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][CH:29]=[CH:30][C:23]=12)[NH2:17].Cl.C(=O)(O)[O-].[Na+]>O.C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([NH:17][C:16]2[CH:18]=[CH:19][C:20]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[NH:28][CH:29]=[CH:30][C:23]=34)=[C:14]([F:13])[CH:15]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

0.209 g (1.12 mmol) of methyl 2-amino-6-chloropyrimidine-4-carboxylate (prepared according to G. Doyle Daves, Fred Baiocchi, Roland K. Robins, and C. C. Cheng, J. Org. Chem., 26 (1961), 2755-2763) and 0.4 g (1.12 mmol) of [3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine (example XIX) are suspended in 5 ml of water and 5 ml of ethanol. 0.11 ml (1.34 mmol) of 37% strength hydrochloric acid is added. The mixture is stirred at 100° C. for 18 hours. After cooling, the mixture is neutralized using an aqueous saturated sodium bicarbonate solution. The resulting precipitate is filtered off with suction and dried. This gives 0.46 g of product (68% of theory).

Workup

temperatureAfter cooling
filtrationThe resulting precipitate is filtered off with suction
customdried

Sources & evidence

ORD record: ord-d374a93459db40659be73da1475c8cba
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737153B2

Reaction notes

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