Water → HCID 19101103, compound

HRID 1975233Notes

Reaction equation

HRID 1975233 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[CH3:6][C:7]([C:10]1[C:15]([OH:16])=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:13]=[C:12]([NH:21][C:22]([NH2:24])=[S:23])[N:11]=1)([CH3:9])[CH3:8].O.C([O-])(O)=O.[Na+]>C(O)C>[CH3:9][C:7]([C:10]1[C:15]([OH:16])=[C:14]([C:17]([CH3:18])([CH3:20])[CH3:19])[N:13]=[C:12]([NH:21][C:22]2[S:23][CH:2]=[C:3]([CH3:4])[N:24]=2)[N:11]=1)([CH3:6])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 19101102HCID 19101102, compound

Product 1

HCID 19101103HCID 19101103, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Chloroacetone (0.17 g, 1.9 mmol) is added to a solution of N-[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]thiourea in 25 mL of ethanol. The reaction mixture is warmed to reflux for 18 hours. The solution is poured into 100 mL of water and the pH is adjusted to 4 with saturated NaHCO3. The resulting precipitate is collected by filtration. Recrystallization from hexane gives 0.26 g (45%) of 4,6-bis(1,1-dimethylethyl)-2-[(4-methyl-2-thiazolyl)amino]-5-pyrimidinol; mp 171°-173° C.

Workup

  1. temperatureThe reaction mixture is warmed
  2. temperatureto reflux for 18 hours
  3. filtrationThe resulting precipitate is collected by filtration
  4. customRecrystallization from hexane

Sources & evidence

ORD record
ord-6fc28580f2d244f2b19092be0221d0cf
Source dataset
uspto-grants-1994_02
Patent number
US05284949

Reaction notes

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