Ethanol → HCID 86760396, compound

HRID 348484Notes

Reaction equation

HRID 348484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([SH:17])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:21][C:22]([NH2:24])=[O:23].[CH2:25](O)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([CH3:25])=[N:15][C:14]([S:17][CH2:21][C:22](=[O:23])[NH2:24])=[N:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6580ChloroacetamideHCID 14798Sodium HydroxideHCID 178522142HCID 178522142, compound

Product 1

HCID 86760396HCID 86760396, compoundYield 70%

Procedure

A solution of 2-mercaptopyrimidine-5-carboxylic acid (4-fluorophenyl)amide (100 mg, 0.38 mmol) in 3 mL of ethanol was treated with aqueous NaOH (3 M, 0.28 mL, 0.84 mmol). A yellow slurry formed, which dissolved over the course of 5 min. An addition of 2-chloroacetamide (53 mg, 0.57 mmol) resulted in the formation of a white slurry. After stirring at ambient temperature for 2.5 h, the reaction was quenched with 50 mL of water and titrated to acidity with 1 M HCl. The slurry was filtered over sintered glass and washed with copious water. Drying in vacuo yielded 85 mg (70%) of 2-carbamoylmethylsulfanyl-4-methylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide. ESI-MS m/z 321 (MH+), 319 (M−H−).

Workup

  1. customA yellow slurry formed
  2. dissolutionwhich dissolved over the course of 5 min
  3. customresulted in the formation of a white slurry
  4. customthe reaction was quenched with 50 mL of water
  5. filtrationThe slurry was filtered over sintered glass
  6. washwashed with copious water
  7. customDrying in vacuo

Sources & evidence

ORD record
ord-a26b5ea72cfc494591a082d96b403570
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

Loading…