Water → HCID 19101103, compound

HRID 1588060Notes

Reaction equation

HRID 1588060 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-991b05a7d127485782a2da71b500566e
Source dataset
uspto-grants-1993_06
Patent number
US05220025

Reaction notes

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