Tetrahydrofuran → Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methanesulfonyl-pyrimidin-4-yl]-amine

HRID 2266074Notes

Reaction equation

HRID 2266074 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].[CH2:26]1COCC1.O[O:32][S:33]([O-:35])=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:33]([CH3:26])(=[O:35])=[O:32])[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 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 1H2O/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-3d3f0c9e15ed4d6a916a114453bdd281
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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