Benzoic Acid → 5-Chloro-2-phenyloxazolo[5,4-d]pyrimidine

HRID 467466Notes

Reaction equation

HRID 467466 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[N:16]=[CH:15][C:14]([NH2:17])=[C:13](Cl)[N:12]=1>O=P(Cl)(Cl)Cl>[Cl:10][C:11]1[N:12]=[CH:13][C:14]2[N:17]=[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:9][C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 2577975-Amino-2,4-dichloropyrimidine

Product 1

HCID 149130905-Chloro-2-phenyloxazolo[5,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

7.82 g (64.0 mmol) benzoic acid and 20 mL POCl3 are stirred together at 100° C. for 30 min. Within 45 min 7.00 g (42.7 mmol) 2,6-dichloro-5-aminopyrimidine are added by several portions. The reaction mixture is stirred for additional 2 h at the same temperature. After that the mixture is carefully added to an ice cold aq. NaOH solution. The resulting precipitate is filtered, washed with water and dried.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e5709728affa4290acf5a33809275cfe
Source dataset
uspto-grants-2014_01
Patent number
US08623860B2

Reaction notes

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