Methanol → 2-Methylsulfonyl-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

HRID 1290665Notes

Reaction equation

HRID 1290665 reaction equation
CS[C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([N+:17]([O-:19])=[O:18])=[C:5]([O:20][C:21]2[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][C:22]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:4]=1.[S:37](S([O-])=O)([O-:40])(=O)=[O:38].[K+].[K+].[CH3:46]O>O1CCOCC1.O>[CH3:46][S:37]([C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:6]([N+:17]([O-:19])=[O:18])=[C:5]([O:20][C:21]2[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][C:22]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:4]=1)(=[O:40])=[O:38]

Participants

6

Reactant 3

HCID 887MethanolHCID 28019Potassium MetabisulfiteHCID 189168492-Methylthio-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

Product 1

HCID 189170172-Methylsulfonyl-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To 2-methylthio-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine (1.82 g, 3.76 mmol) in 40 mL MeOH and 40 mL dioxane at 0° C. was added potassium metabisulfite (KHSO5) (3.59 g, 11.3 mmol) in 40 mL water. The suspension was allowed to warm to ambient temperature and stirred for 15 hours. The reaction was concentrated to 25 mL and extracted with methylene chloride (200 mL). The organic layer was dried (Na2 SO4), evaporated and chromatographed on silica gel (2:1, hexane/ethyl acetate) to afford 0.26 g of 2-methylsulfonyl-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (F), as a white solid.

Workup

  1. concentrationThe reaction was concentrated to 25 mL
  2. extractionextracted with methylene chloride (200 mL)
  3. customThe organic layer was dried (Na2 SO4)
  4. customevaporated
  5. customchromatographed on silica gel (2:1, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5bd181a5366c495a9d3eff54b8cce9c1
Source dataset
uspto-grants-1998_05
Patent number
US05753635

Reaction notes

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