Sodium methanesulfinate → Benzyl 3-[4-(5-methanesulfonyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate

HRID 1027715Notes

Reaction equation

HRID 1027715 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:31]=[C:30]([CH3:32])[C:14]([O:15][CH:16]4[CH2:19][CH:18]([C:20]([O:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:21])[CH2:17]4)=[C:13]([CH3:33])[CH:12]=3)[O:8][C:6]=2[N:7]=1.[CH3:34][S:35]([O-:37])=[O:36].[Na+]>CN(C)C=O>[CH3:34][S:35]([C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:31]=[C:30]([CH3:32])[C:14]([O:15][CH:16]4[CH2:19][CH:18]([C:20]([O:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:21])[CH2:17]4)=[C:13]([CH3:33])[CH:12]=3)[O:8][C:6]=2[N:7]=1)(=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 86675955Benzyl 3-[4-(5-chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate

Product 1

HCID 71203355Benzyl 3-[4-(5-methanesulfonyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 200 mg of benzyl 3-[4-(5-chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]cyclobutanecarboxylate and 48 mg of sodium methylsulfinate in 4 ml of N,N-dimethylformamide was heated in a microwave reactor at 100° C. for 60 min. At room temperature, the mixture was filtered and then washed with DMF. The filtrate was concentrated and the resulting residue was purified by preparative HPLC. This gave 71 mg (32%) of the title compound.

Workup

  1. filtrationAt room temperature, the mixture was filtered
  2. washwashed with DMF
  3. concentrationThe filtrate was concentrated
  4. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a3b2f8ceaec541b2af4467a93cb6f73a
Source dataset
uspto-grants-2014_05
Patent number
US08735402B2

Reaction notes

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