Hexane → HCID 54479191, compound

HRID 1588061Notes

Reaction equation

HRID 1588061 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([NH:16][C:17]([NH2:19])=[S:18])[N:6]=1)([CH3:4])[CH3:3].C([CH:22](Br)[C:23](=O)[C:24]([O-:26])=[O:25])C.[CH3:29][CH2:30]CCCC>C(O)C.O>[CH2:29]([O:26][C:24]([C:23]1[N:19]=[C:17]([NH:16][C:7]2[N:8]=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=2)[S:18][CH:22]=1)=[O:25])[CH3:30]

Participants

6

Reactant 3

HCID 8058HexaneHCID 19101102HCID 19101102, compoundHCID 21948992Ethylbromopyruvate

Product 1

HCID 54479191HCID 54479191, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]thiourea (1.0 g, 3.5 mmol) is added to a solution of ethylbromopyruvate (0.72 g, 3.7 mmol) in 25 mL of ethanol. The mixture is warmed to reflux for 4.5 hours, then diluted with 100 mL of water. The pH of the solution is adjusted to 4 with saturated NaCHO3. The resulting precipitate is collected by filtration and recrystallized from ethanol/water. Yield of 2-([4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]amino)-4-thiazolecarboxylic acid ethyl ester is 0.86 g (65%). An analytical sample was obtained by treating an aliquot with boiling hexane for 10 minutes; mp 204°-206° C.

Workup

  1. temperatureThe mixture is warmed
  2. temperatureto reflux for 4.5 hours
  3. filtrationThe resulting precipitate is collected by filtration
  4. customrecrystallized from ethanol/water
  5. customAn analytical sample was obtained

Sources & evidence

ORD record
ord-3da5348c6a4f4f7db035f16dcd861531
Source dataset
uspto-grants-1993_06
Patent number
US05220025

Reaction notes

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