Ethanol → HCID 22385757, compound

HRID 895138Notes

Reaction equation

HRID 895138 reaction equation
C(OC(O[CH2:8][CH3:9])CBr)C.C(O)C.C(=O)([O-])O.[Na+].[NH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21][N:20]=1>Br.O>[CH3:25][C:23]1[N:22]=[CH:21][N:20]2[CH:8]=[CH:9][N:18]=[C:19]2[CH:24]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium BicarbonateHCID 5728526-Methylpyrimidin-4-amine

Product 1

HCID 22385757HCID 22385757, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A stirred mixture of bromoacetaldehyde diethyl acetal (3.43 ml, 22.1 mmol) in concentrated hydrobromic acid (1.1 ml) and water (1.1 ml) was heated at reflux under nitrogen for 2 h, then poured into ethanol (57 ml). The solution was neutralised to pH 7 with solid sodium hydrogen carbonate, then filtered. To the filtrate was added 4-amino-6-methylpyrimidine (1.0063 g, 9.22 mmol) and the mixture was stirred at room temperature for 30 min then at 60° C. for 19 h. After allowing to cool, the solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2CO2) to give 0.5071 g (41%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 2.54 (3H, s), 7.33 (1H, s), 7.59 (1H, s), 7.62 (1H, d, J 1.2 Hz), 8.96 (1H, s); MS (ES+) m/z 134 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2 h
  3. filtrationfiltered
  4. waitat 60° C. for 19 h
  5. temperatureto cool
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2CO2)

Sources & evidence

ORD record
ord-0a3ff447616d480d963ee31ba017ec82
Source dataset
uspto-grants-2005_07
Patent number
US06914065B2

Reaction notes

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