4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine → 2-Chloro-6-(4,6-dimethoxy-2-pyrimidinyloxy)aniline

HRID 1493803Notes

Reaction equation

CC(C)([O-])C.[K+].Br.[Cl:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:10]=1[NH2:11].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1>CN(C)C=O>[Cl:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:21]2[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=2)[C:10]=1[NH2:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium t-butoxide (22.4 g) was added portionwise to stirred, cooled 2-chloro-6-hydroxyaniline hydrobromide (22.5 g) in dimethylformamide (100 ml) under nitrogen. After 10 minutes, 4,6-dimethoxy-2-methylsulphonyl pyrimidine (21.8 g) was added, and the mixture was heated at 80° C. with stirring for 22 hours. After addition to ice/water, the precipitated solid was separated by filtration, washed thoroughly with water, dried and recrystallised from isopropanol yielding 17.5 g of the desired product, mp 84°-86° C. Reduction in volume of the mother liquors gave a further 0.85 g of product, mp 86°-87° C.

Workup

stirringwith stirring for 22 hours
customthe precipitated solid was separated by filtration
washwashed thoroughly with water
customdried
customrecrystallised from isopropanol yielding 17.5 g of the desired product, mp 84°-86° C

Sources & evidence

ORD record: ord-410bf12b2ae547de94157260885078c6
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05024693

Reaction notes

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