Phenyl chloroformate → phenyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]carbamate

HRID 2353697Notes

Reaction equation

HRID 2353697 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([C:19]2[S:23][C:22]([NH2:24])=[N:21][CH:20]=2)[N:9]=1.C(=O)([O-])O.[Na+].Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>O1CCOCC1>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([C:19]2[S:23][C:22]([NH:24][C:31](=[O:32])[O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:21][CH:20]=2)[N:9]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 593799205-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-amine

Product 1

HCID 59380033phenyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-amine (1 g, 2.71 mmol), sodium hydrogen carbonate (342 mg), and phenyl chloroformate (0.511 mL) in dioxane was stirred at RT for 2 hours then concentrated in vacuo. The residue was partitioned between DCM and water and the organic layer dried over sodium sulphate and evaporated to give a foam. The foam was triturated with a mixture of hexane and diethyl ether to give the desired material as a white solid (1.1 g).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. dry with materialthe organic layer dried over sodium sulphate
  4. customevaporated
  5. customto give a foam
  6. customThe foam was triturated with a mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-123f072cc6ad400491b8f38a5040c51c
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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