4,6-Dichloro-2-(methylthio)pyrimidine → (S)-4-(6-chloro-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholine

HRID 1771524Notes

Reaction equation

HRID 1771524 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:20][C@H:21]1[CH2:26][O:25][CH2:24][CH2:23][NH:22]1>C(Cl)Cl>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][C@@H:21]2[CH3:20])[CH:7]=1

Participants

5

Reactant 3

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 86691142(S)-4-(6-chloro-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineYield 109.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4,6-dichloro-2-(methylthio)pyrimidine (585 mg, 3.0 mmol) in DCM (5 mL) was added DIPEA (1.5 mL, 9.0 mmol), followed by 3-(S)-methylmorpholine (909 mg, 9.0 mmol) dropwise. The reaction mixture was stirred at 40° C. overnight whereupon it was washed with water (10 mL), passed through a PTFE hydrophobic frit and the solvent removed in vacuo to yield a colourless oil (850 mg) used without further purification.

Workup

  1. washwas washed with water (10 mL)
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e83738940c1c4c7b867e93d63e41c448
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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