Water → HCID 67250367, compound

HRID 2420984Notes

Reaction equation

HRID 2420984 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([C:16]([OH:18])=O)=[CH:5][N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:32][NH2:33].O>C1COCC1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([C:16]([NH:32][NH2:33])=[O:18])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 67250020HCID 67250020, compound

Product 1

HCID 67250367HCID 67250367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methylthio-4-(2-trimethylsilylethoxy)pyrimidine-5-carboxylic acid (9.73 g) obtained in Step 2 was dissolved in THF (100 mL), carbonyldiimidazole (5.5 g) was added thereto, followed by stirring at room temperature for 1.5 hours. Then, hydrazine monohydrate (4.70 mL) was added dropwise to the reaction mixture, and the resulting mixture was stirred at room temperature for 2.5 hours. After completion of the reaction was confirmed by thin-layer chromatography, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was sequentially washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the mixture was dried under reduced pressure to give crude 2-methylthio-4-(2-trimethylsilylethoxy)pyrimidine-5-carbohydrazide [Compound (E) in which R1 is 2-trimethylsilylethoxy].

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2.5 hours
  2. additionwas added to the reaction mixture
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was sequentially washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe mixture was dried under reduced pressure

Sources & evidence

ORD record
ord-c3bf5320a68a416dae1df7ddf5f71815
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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