Morpholine → HCID 22397154, compound

HRID 411191Notes

Reaction equation

HRID 411191 reaction equation
Br[CH2:2][C:3]1[S:17][C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10](=[O:11])[N:5]2[CH:4]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CN(C=O)C.C(Cl)Cl>[N:18]1([CH2:2][C:3]2[S:17][C:6]3=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10](=[O:11])[N:5]3[CH:4]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 22397189HCID 22397189, compound

Product 1

HCID 22397154HCID 22397154, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-(bromomethyl)-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate (Preparation 9, 159 mg) and morpholine (0.5 mL) in DMF (10 mL) is stirred for 4 h at rt. The mixture is diluted with CH2Cl2 (100 mL) and is washed with water. The organic layer is dried (MgSO4) and concentrated to afford 130 mg (80%) of the title compound as a white solid. Physical characteristics: MS (ESI+) m/z 324 (M+H)+. 1H NMR (DMSO) δ 8.62, 8.22,4.25, 3.75, 3.59, 2.49, 1.28.

Workup

  1. washis washed with water
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-00a0b48a4d7e4987b41cb5553efea913
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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