Oxolane--water (1/1) → Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amine

HRID 81748Notes

Reaction equation

HRID 81748 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[CH:21]([CH3:23])[CH3:22])=[CH:8][N:7]=[C:6](SC)[N:5]=1)[CH3:2].O.[CH2:27]1COCC1.O[O:33][S:34]([O-:36])=O.[K+]>O>[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[CH:21]([CH3:22])[CH3:23])=[CH:8][N:7]=[C:6]([S:34]([CH3:27])(=[O:36])=[O:33])[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 21881883Oxolane--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 59598719Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amine

Product 1

HCID 59598536Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amineYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amine (0.129 g, 0.4 mmol) in 20 mL 1:1 H2O/THF was added OXONE® (0.461 g, 0.8 mmol) in 4.0 mL H2O. After 2 hours, 50 mL H2O was added and the mixture was extracted with ethyl acetate, washed with H2O and washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amine (0.131 g, 92%) as a white foam.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with H2O
  3. washwashed with brine
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3a132353c7c4cb4b46f2289c639ad83
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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