2,5-dichloro-N-methylpyrimidin-4-amine → Methyl 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoate

HRID 2403471Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH:13]([F:15])[F:14].Cl[C:17]1[N:22]=[C:21]([NH:23][CH3:24])[C:20]([Cl:25])=[CH:19][N:18]=1.Cl.O1CCOCC1>C(O)CCC>[Cl:25][C:20]1[C:21]([NH:23][CH3:24])=[N:22][C:17]([NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[O:12][CH:13]([F:14])[F:15])=[N:18][CH:19]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 4-amino-3-(difluoromethoxy)benzoate (70 mg), 2,5-dichloro-N-methylpyrimidin-4-amine, 0.1 mL of 4N HCl/dioxane and 1 mL of n-butanol were placed in a microwave vial. The reaction was heated for 30 minutes at 150° C. and monitored by LCMS. The mixture was concentrated and purified by silica gel chromatography to give 100 mg of pure methyl 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoate.

Workup

concentrationThe mixture was concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-e6d80583ddac40c9a1e79435cce7558c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802674B2

Reaction notes

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