Methanol → Methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

HRID 655330Notes

Reaction equation

HRID 655330 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])=[N:10][CH:11]=1.[CH3:21]O>>[OH:5][C:6]1[CH:11]=[N:10][C:9]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([O:17][CH3:21])=[O:16])=[N:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride3×HCID 594849363-(5-Hydroxypyrimidin-2-yl)benzoic acid

Product 1

HCID 59438048Methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

Conditions

Temperature
80 °C

Procedure

32.7 ml (445 mmol) of thionyl chloride are added to a suspension of 88.0 g (366 mmol) of 3-(5-hydroxypyrimidin-2-yl)benzoic acid in 1.4 l of methanol, and the mixture is heated at 80° C. for 2 hours. 20 ml (276 mmol) of thionyl chloride and, after 2 hours, a further 10 ml (138 mmol) of thionyl chloride are then added. After each addition, the reaction mixture is stirred at 80° C. for 2 hours. The reaction mixture is concentrated to a volume of about 300 ml in vacuo. The resultant precipitate is filtered off and dried in vacuo: methyl 3-(5-hydroxypyrimidin-2-yl)benzoate as brownish crystals; m.p. 219-223° C., ESI 231 (M+H); HPLC: Rt=3.87 min (method C).

Workup

  1. additionAfter each addition
  2. concentrationThe reaction mixture is concentrated to a volume of about 300 ml in vacuo
  3. filtrationThe resultant precipitate is filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bb83781a4883486b99616f228cf41ca3
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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