Bromine → 6-Bromo-2-chloro-5-phenyl-thieno[2,3-d]pyrimidine

HRID 928585Notes

Reaction equation

HRID 928585 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[Br:17]Br.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>C(O)(=O)C>[Br:17][C:9]1[S:8][C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 54670067L-Ascorbic AcidHCID 821046552-Chloro-5-phenylthieno[2,3-d]pyrimidine

Product 1

HCID 895794776-Bromo-2-chloro-5-phenyl-thieno[2,3-d]pyrimidineYield 85.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Chloro-5-phenyl-thieno[2,3-d]pyrimidine (0.5 g, 2.03 mmol) was stirred in acetic acid (10 mL). Bromine (0.65 g, 0.21 mL, 4.06 mmol) was added dropwise and the reaction allowed to stir at room temperature over the weekend. The reaction mixture was poured into saturated aqueous ascorbic acid solution. The resulting solid was filtered off and dried in vacuo at 40° C. to afford 6-bromo-2-chloro-5-phenyl-thieno[2,3-d]pyrimidine (567 mg).

Workup

  1. filtrationThe resulting solid was filtered off
  2. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-17503121418a4bf3b97873b120732459
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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