Dimethyl Sulfide → Tert-butyl (6-formylpyrimidin-4-yl)carbamate

HRID 2366180Notes

Reaction equation

HRID 2366180 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:4]=1)=C.[O:17]=[O+][O-].CSC>CO>[CH:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:4]=1)=[O:17]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 66803845tert-Butyl 6-vinylpyrimidin-4-ylcarbamate

Product 1

HCID 23593604Tert-butyl (6-formylpyrimidin-4-yl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 6-vinylpyrimidin-4-ylcarbamate (4.4 g, 0.020 mol) in MeOH (200 mL) at −78° C. was bubbled O3 for 1 hour. N2 was bubbled through the mixture for 10 minutes and then dimethylsulfide (1.24 g, 0.020 mol) was added dropwise. After addition, the solvent was removed under reduced pressure to give the crude desired product (4.6 g, over 100% yield) which was used in the next step without purification. LCMS (ESI) m/z: 224.1 [M+H+].

Workup

  1. customN2 was bubbled through the mixture for 10 minutes
  2. additionAfter addition
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c9205ca227c944c2bba0a5074dd9ef68
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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