Methyl Isocyanate → HCID 70026654, compound

HRID 1060867Notes

Reaction equation

HRID 1060867 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:22]([OH:25])[CH2:23][CH3:24])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:6]=2[N:7]=1.[CH3:26][N:27]=[C:28]=[O:29].CN(C1C=CC=CN=1)C>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([CH:22]([O:25][C:28](=[O:29])[NH:27][CH3:26])[CH2:23][CH3:24])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=3[CH3:19])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 12228Methyl Isocyanate2×HCID 218852-DimethylaminopyridineHCID 69893475HCID 69893475, compound

Product 1

HCID 70026654HCID 70026654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-propan-1-ol(62 mg, 0.184 mmol), methyl isocyanate (0.25 ml), dimethylaminopyridine (20 mg) in dichloromethane (2 ml) was heated at reflux for 1 hr. Additional methyl isocyanate (0.25 ml) was added and the resulting mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with chloroform. The organic layer was separated, dried and concentrated to give a yellow foam (95 mg). The foam was purified by preparative thin layer chromatography plate in 10% methanol in chloroform, then in 20% methanol in chloroform as solvent to give the title compound (29 mg) as an off-white solid.

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-a55cda6ec2e04e109f4461b252fe38f9
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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