Methyl Isocyanate → HCID 10178080, compound

HRID 1060868Notes

Reaction equation

HRID 1060868 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:21]([OH:24])[CH2:22][CH3:23])[C:5]2[CH2:10][O:9][CH2:8][N:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]=2[N:20]=1.[CH3:25][N:26]=[C:27]=[O:28].CN(C1C=CC=CN=1)C>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([CH:21]([O:24][C:27](=[O:28])[NH:26][CH3:25])[CH2:22][CH3:23])[C:5]2[CH2:10][O:9][CH2:8][N:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]=2[N:20]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 218852-DimethylaminopyridineHCID 12970218HCID 12970218, compound

Product 1

HCID 10178080HCID 10178080, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[7-methyl-1-(2,4,6-trimethyl-phenyl)-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-5-yl]-propan-1-ol (50 mg), methyl isocyanate (0.25 ml), dimethylaminopyridine (37 mg) in dichloromethane (2 ml) was heated at reflux for 1 hr. The mixture was quenched with water and extracted with chloroform. The organic layer was separated, dried and concentrated to give a clear oil (70 mg). The oil was purified by silica gel thin layer chromatography plate using 40% ethyl acetate in hexane as solvent to give 36 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. customThe mixture was quenched with water
  4. extractionextracted with chloroform
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b75091e4e1c84762b8c2f131e907fe60
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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