Water → HCID 67251657, compound

HRID 2420982Notes

Reaction equation

HRID 2420982 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][CH2:11][CH3:12])[C:6]([C:13]([OH:15])=O)=[CH:5][N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:29][NH2:30].O>C1COCC1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][CH2:11][CH3:12])[C:6]([C:13]([NH:29][NH2:30])=[O:15])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 20562038HCID 20562038, compound

Product 1

HCID 67251657HCID 67251657, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methylthio-4-n-propylaminopyrimidine-5-carboxylic acid (22.6 g) obtained in Step 1 was dissolved in THF (360 mL), then carbonyldiimidazole (16.9 g) was added thereto, followed by stirring at room temperature for 1.5 hours. Then, a THF (100 mL) solution of hydrazine monohydrate (14.5 mL) was added dropwise to the reaction mixture over 30 minutes, followed by stirring 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. Precipitated crystals were collected by filtration and the resulting crystals were washed with water and dried thoroughly under reduced pressure to give 2-methylthio-4-n-propylaminopyrimidine-5-carbohydrazide (20.1 g, yield 84%).

Workup

  1. stirringby stirring at room temperature for 2.5 hours
  2. additionwas added to the reaction mixture
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washthe resulting crystals were washed with water
  6. customdried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-9be822f8868344e4bf11e87c5036cc3c
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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