Water → Methyl 4-(2-(4-morpholinophenylamino)pyrimidin-4-ylthio)benzoate

HRID 81710

Reaction equation

Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>O1CCOCC1>[O:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:26]=[CH:27][C:28]([NH:29][C:2]3[N:7]=[C:6]([S:8][C:9]4[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=4)[CH:5]=[CH:4][N:3]=3)=[CH:30][CH:31]=2)[CH2:23][CH2:24]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred mixture of methyl 4-(2-chloropyrimidin-4-ylthio)benzoate (3.80 g, 14 mmol) and 4-morpholinoaniline (2.89 g, 16 mmol) in 1,4-dioxane (100 mL), was added p-toluensulfonic acid monohydrate (2.57 g, 14 mmol) in one portion. The whole was heated at 100° C. for 16 hours, cooled to room temperature, and poured into water (200 mL). The precipitate was collected by filtration, washed repeatedly with 2% aqueous citric acid, water, and ethyl acetate. It was then dried under high vacuum to afford the product (2.90 g, 51%).

Workup

temperaturecooled to room temperature
filtrationThe precipitate was collected by filtration
washwashed repeatedly with 2% aqueous citric acid, water, and ethyl acetate
customIt was then dried under high vacuum

Sources & evidence

ORD record: ord-3c4727d9735b4590a448c257b4c2608f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846704B2

Linked notes

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