Phenol → HCID 136097745, compound

HRID 2059863Notes

Reaction equation

HRID 2059863 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17](=O)[CH2:18][C:19](OCC)=[O:20])=[CH:11][CH:10]=1.C1(O)C=CC=CC=1>C([O-])(O)=O.[Na+]>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][CH2:16][C:17]2[N:7]=[CH:5][NH:6][C:19](=[O:20])[CH:18]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 160693Formamidine acetateHCID 15050275HCID 15050275, compound

Product 1

HCID 136097745HCID 136097745, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of formamidine acetate (1508 mg, 14.48 mmol), ethyl 4-(4-chlorophenylthio)-3-oxobutanoate Part A (790 mg, 2.90 mmol) and phenol (8178 mg, 87 mmol) was stirred at 140° C. for 18 hours. After the reaction cooled to RT, the mixture was diluted with saturated NaHCO3 (65 mL) and extracted with EtOAc (80 mL). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient, using LC-MS to identify fractions containing the desired product) to afford 6-((4-chlorophenylthio)-methyl)pyrimidin-4(3H)-one 10B (169 mg, 22% yield). 1H NMR (400 MHz, CD3OD) δ ppm 7.97 (1H, s), 7.07-7.25 (4H, m), 6.06 (1H, s), 3.80 (2H, s).

Workup

  1. temperatureAfter the reaction cooled to RT
  2. extractionextracted with EtOAc (80 mL)
  3. dry with materialThe EtOAc layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient
  6. additioncontaining the desired product)

Sources & evidence

ORD record
ord-e10fa67c1a2543278d0da7d4ca153dce
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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