Phenyl chloroformate → Phenyl (4-{4-[1-methyl-1-(methylsulfonyl)ethyl]-6-morpholin-4-ylpyrimidin-2-yl}phenyl)carbamate

HRID 2353668Notes

Reaction equation

HRID 2353668 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[N:9]=1)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].C(=O)(O)[O-].[Na+].Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34]>O1CCOCC1>[CH3:3][C:2]([C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:33](=[O:34])[O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:24][CH:25]=2)[N:9]=1)([S:4]([CH3:7])(=[O:5])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380029(4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-morpholin-4-ylpyrimidin-2-yl}phenyl)amine

Product 1

HCID 86621594Phenyl (4-{4-[1-methyl-1-(methylsulfonyl)ethyl]-6-morpholin-4-ylpyrimidin-2-yl}phenyl)carbamateYield 35.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-morpholin-4-ylpyrimidin-2-yl}phenyl)amine (1.5 g, 3.98 mmol) was dissolved in dioxane (15 mL). Sodium bicarbonate (503 mg, 5.98 mmol) was added, followed by phenyl chloroformate (0.502 mL, 3.98 mmol) and the reaction stirred at room temperature for 2 hours. The solvent was removed in vacuo, and the resultant oil partitioned between 20 mL DCM and 20 mL water. The organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. The cream solid obtained was chromatographed on silica, eluting with 0-50% ethyl acetate in DCM, to give the desired material as a white solid (700 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resultant oil partitioned between 20 mL DCM and 20 mL water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe cream solid obtained
  7. customwas chromatographed on silica
  8. washeluting with 0-50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-9d3cc9f3e3964a619f0e1fc237b00d09
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…