Hydrochloric Acid → 4-(Propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid

HRID 2284634Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([NH:21][CH2:22][CH2:23][CH3:24])=[N:8][C:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[N:10][CH:11]=1)=[O:5])C.C(O)C.[OH-].[Na+].Cl>O1CCCC1>[CH2:22]([NH:21][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[N:8]=1)[CH2:23][CH3:24]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid ethyl ester (A2, 9.2 g), ethanol (115 mL), tetrahydrofuran (58 mL) and 2.0 mol/L aqueous sodium hydroxide (115 mL) was stirred at 40° C. for 4 hours, and then further stirred at 60° C. for 3 hours. The reaction mixture was cooled to room temperature, then 12 mol/L aqueous hydrochloric acid (19.5 mL) was added to the mixture (pH 5 to 6), and the organic solvent was evaporated under reduced pressure. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid (A3, 9.3 g) as white solid.

Workup

stirringfurther stirred at 60° C. for 3 hours
temperatureThe reaction mixture was cooled to room temperature
customthe organic solvent was evaporated under reduced pressure
filtrationThe solid matter was taken by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-c1989e22193245d4bb900c5a742cf3db
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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