Phosphorus oxychloride → 6-Bromo-4-chlorothieno[2,3-d]pyrimidine

HRID 240570Notes

Reaction equation

HRID 240570 reaction equation
[Br:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](O)[C:4]=2[CH:3]=1.P(Cl)(Cl)([Cl:14])=O.C([O-])(O)=O.[Na+]>>[Br:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:14])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178518066HCID 178518066, compound

Product 1

HCID 122252616-Bromo-4-chlorothieno[2,3-d]pyrimidineYield 83%

Conditions

Temperature
80 °C

Procedure

To 6-bromothieno[2,3-d]pyrimidin-4-ol (3.0 g, 19.7 mmol) was added phosphorus oxychloride (5 mL). After heating to 80° C. for 1.5 hours, the reaction mixture was poured into saturated NaHCO3 and ice. The solid was filtered, washed with water and dried to provide the product (4.06 g, 83%) as brown solid.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-7f3e5b497c8541b392a0a31a53cb64bf
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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