Dimethylformamide → HCID 69924352, compound

HRID 1005981Notes

Reaction equation

HRID 1005981 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25]N(C)C=O.CI>>[C:1]([O:5][C:6](=[O:24])[N:7]([CH3:25])[C:8]1[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 69926284HCID 69926284, compound

Product 1

HCID 69924352HCID 69924352, compoundYield 98%

Procedure

To a solution of 1.60 g (4.61 mmol) (2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester in 20 ml N,N-dimethylformamide 0.25 g (6.4 mmol) sodiumhydride (60% dispersion in mineraloil) was added and the reaction mixture stirred for 1 h. After the addition of 0.48 ml (7.83 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. The reaction mixture was poured into 100 ml ice-water and three times extracted with 80 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1) to give 1.60 g (98%) methyl-(2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert-butyl ester as a colorless oil, MS (EI): 361 (M+)

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs
  2. extractionextracted with 80 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-79de9d45c0664568ab714820133d0312
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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