Methyl Isocyanate → HCID 22004635, compound

HRID 324371Notes

Reaction equation

HRID 324371 reaction equation
[CH2:1]([N:8]([C:13]1[N:18]=[C:17]([CH3:19])[N:16]=[C:15]2[N:20]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=3[Cl:33])[N:21]=[C:22]([S:23][CH3:24])[C:14]=12)[CH2:9][CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:36][N:37]=[C:38]=[O:39]>C1COCC1>[CH3:36][NH:37][C:38]([O:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:13]1[N:18]=[C:17]([CH3:19])[N:16]=[C:15]2[N:20]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=3[Cl:33])[N:21]=[C:22]([S:23][CH3:24])[C:14]=12)=[O:39]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 24758Sodium hydrideHCID 22004591HCID 22004591, compound

Product 1

HCID 22004635HCID 22004635, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{benzyl-[6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-propan-1-ol (100 mg, 0.191 mmol) in 2 ml of dry THF was treated with 6 mg of 60% sodium hydride in oil and methyl isocyanate (39 mg, 6.78 mmol) at room temperature and stirred at room temperature for 10 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 110 mg of white form. The form was purified through silica gel column chromatography to give 79 mg of the title compound as a white glass form. 1H NMR (CDCl3): 2.03(m,2H), 2.51(s,3H), 2.59(s,3H), 2.77(d,3H), 3.79(t,2H), 4.12(t,2H), 4.50(brs,1H), 5.17(s,2H), 7.2-7.45(m,5H), 7.51(s,2H)ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give 110 mg of white form
  6. customThe form was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-492c6f93fd104c81835e4b2b4704a329
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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