2,6-Dimethylmorpholine, cis- → HCID 69088090, compound

HRID 2278431Notes

Reaction equation

HRID 2278431 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:11][C@H:12]1[O:17][C@@H:16]([CH3:18])[CH2:15][NH:14][CH2:13]1>>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([N:14]2[CH2:13][C@H:12]([CH3:11])[O:17][C@H:16]([CH3:18])[CH2:15]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6415002,6-Dimethylmorpholine, cis-HCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 69088090HCID 69088090, compoundYield 64.1%

Conditions

Temperature
45 °C

Procedure

To a solution of 5-bromo-2-chloro-4-methoxypyrimidine (17.2 g, 77 mmol) stirred in air at 0° C. was added neat cis-2,6-dimethylmorpholine (24.5 g, 213 mmol) dropwise in 10 minutes. The reaction mixture was stirred at 45° C. for 30 minutes. The organic phase was evaporated in vacuo to give the crude product as a white solid. The crude product was added to a silica gel column and was eluted with hexane/ethyl acetate (20/1). Collected fractions were evaporated to give the title compound as white solid (17.4 g, 49.3 mmol, 64.1% yield). LC/MS [M+H]+=302/304.

Workup

  1. customThe organic phase was evaporated in vacuo
  2. customto give the crude product as a white solid
  3. washwas eluted with hexane/ethyl acetate (20/1)
  4. customCollected fractions were evaporated

Sources & evidence

ORD record
ord-ac04d07e43f84b9abbf87d8ca70c10fd
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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