Ammonia → 4-Amino-6-chloro-N-(3-methoxybenzyl)pyrimidine-5-carboxamide

HRID 1052458Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:21]>O1CCOCC1>[NH2:21][C:6]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4,6-Dichloro-N-(3-methoxybenzyl)pyrimidine-5-carboxamide (523 mg, 1.68 mmol) was dissolved in dioxane (8 ml) and cooled in an ice bath. Ammonia solution (1.2 ml, 8.40 mmol, 7N in MeOH) was added dropwise and the mixture was stirred at 0° C. for 6 h. After evaporation of the solvent under reduced pressure, the residue was suspended in ethyl acetate and filtered, washing several times with ethyl acetate. The organics were evaporated under reduced pressure to yield the final compound as a solid (424 mg, 97% purity, 84% yield) which was used in the next synthetic step without further purification.

Workup

temperaturecooled in an ice bath
customAfter evaporation of the solvent under reduced pressure
filtrationfiltered
washwashing several times with ethyl acetate
customThe organics were evaporated under reduced pressure

Sources & evidence

ORD record: ord-6b2bbe990e4f406b8de1a594acba2695
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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