Benzoyl chloride → 7-chloro-2-phenyl[1,3]oxazolo[5,4-d]pyrimidine

HRID 1678031Notes

Reaction equation

HRID 1678031 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[Cl:8][C:7]1[C:2]2[N:1]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:17][C:3]=2[N:4]=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 2831667-chloro-2-phenyl[1,3]oxazolo[5,4-d]pyrimidineYield 77.6%

Procedure

A mixture of 5-amino-4,6-dichloropyrimidine (1.05 g, 0.00640 mol) and benzoyl chloride (0.89 mL, 0.0077 mol) was subjected to microwave irradiation (100° C.) for 2 hours. The reaction was cooled and the residue was triturated with diethyl ether, filtered and collected to obtain 1.15 g (77.5%) of a yellow solid. LC/MS: Rt=1.84 min, ES+ 232.19 (AA standard).

Workup

  1. customwas subjected to microwave irradiation (100° C.) for 2 hours
  2. temperatureThe reaction was cooled
  3. customthe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. customcollected

Sources & evidence

ORD record
ord-6952a04e770f4b11bce9141e0951c5c6
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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