Triethylamine → 2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine

HRID 2353624Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=1.C(N(CC)CC)C.[CH3:21][C@H:22]1[CH2:27][O:26][CH2:25][CH2:24][NH:23]1>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][C@@H:22]2[CH3:21])[CH:5]=[C:4]([CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=1

Participants

Conditions

Temperature: -5 °C

Procedure

2,4-Dichloro-6-(methylsulfonylmethyl)pyrimidine (30 g, 0.13 mol) was dissolved in dichloromethane and stirred (under nitrogen) at −5° C. Triethylamine (17.4 mL, 0.13 mol) was added to give a clear brown solution. (3S)-3-Methylmorpholine was dissolved in dichloromethane and added dropwise keeping the reaction below −5° C. The cooling bath was then removed and the mixture stirred for 1 hour. The reaction mixture was heated at reflux for 2 hours, then the reaction mixture was washed with water, dried then evaporated. The crude material was purified by preparative HPLC to give the desired material as a solid (19.3 g).

Workup

customto give a clear brown solution
additionadded dropwise
customthe reaction below −5° C
customThe cooling bath was then removed
stirringthe mixture stirred for 1 hour
temperatureThe reaction mixture was heated
temperatureat reflux for 2 hours
washthe reaction mixture was washed with water
customdried
customthen evaporated
customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-15e04a46fb6c4a3c958399ad3698ee54
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750003B2

Reaction notes

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