Hydrochloric Acid → 2-((4-Carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid

HRID 2284651Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[C:14]([C:21]([O:23]CC)=[O:22])=[CH:13][N:12]=2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Cl>O1CCCC1.CO.O.[OH-].[Na+]>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[C:14]([C:21]([OH:23])=[O:22])=[CH:13][N:12]=2)=[CH:8][CH:9]=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (C1, 8.0 g) in tetrahydrofuran (240 mL) and methanol (240 mL), water (40 mL) and 5.0 mol/L aqueous sodium hydroxide (48 mL) were added at room temperature, and the mixture was stirred at 60° C. for 3 hours. The reaction mixture was cooled on ice, then 12 mol/L aqueous hydrochloric acid was added to the mixture until pH of the mixture became 2, and the reaction mixture was poured into ice water (2000 mL). The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid (C2, 4.0 g) as white solid.

Workup

temperatureThe reaction mixture was cooled on ice
filtrationThe solid matter was taken by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-69d8e2859dae42fea4ad7417426c3b76
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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