Water → 6-Amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylic acid

HRID 249663Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([OH:17])=[O:16])[CH:3]=1.[Cl:18]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[N:5]=[C:4]([C:15]([OH:17])=[O:16])[C:3]=1[Cl:18]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 6-amino-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid (i.e. the product of Step B) (75 g, 300 mmol) in N,N-dimethylformamide (300 mL) at 50° C. was added portionwise N-chlorosuccinimide (44.1 g, 330 mmol). The temperature of the reaction mixture increased exothermically to 65° C. Then the reaction mixture was heated at 55° C. for 3 h. Additional N-chlorosuccinimide (14 g, 90 mmol) was added portionwise, and the reaction mixture was maintained at 55° C. for 30 minutes. After the reaction mixture was cooled water was added. The resulting solid was isolated by filtration, washed with water, dissolved in ethyl acetate, washed with water and dried. The solvent was removed using a rotary evaporator to afford the title product, a compound of the present invention, as a tan solid (73.68 g).

Workup

temperatureThen the reaction mixture was heated at 55° C. for 3 h
temperaturethe reaction mixture was maintained at 55° C. for 30 minutes
additionwas added
customThe resulting solid was isolated by filtration
washwashed with water
dissolutiondissolved in ethyl acetate
washwashed with water
customdried
customThe solvent was removed
customa rotary evaporator

Sources & evidence

ORD record: ord-8771eef4f9134e969b606860399eab85
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863220B2

Reaction notes

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