Phosphorus oxychloride → 4-Chloro-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine

HRID 1641339Notes

Reaction equation

HRID 1641339 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16](O)[C:17]4[S:22][CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:16]1[C:17]2[S:22][CH2:21][CH2:20][C:18]=2[N:19]=[C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)[N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517892HCID 178517892, compound

Product 1

HCID 594759174-Chloro-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidineYield 86.4%

Procedure

12.95 g 2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ol and 50.89 ml (546 mmol) phosphorus oxychloride are heated for 4 hours to 120° C. Then the reaction mixture is evaporated down, the residue is mixed with water. The precipitate formed is suction filtered, washed with water and dried. The crude product is stirred with methanol and suction filtered. 11.78 g of the product are obtained as a powder.

Workup

  1. customThen the reaction mixture is evaporated down
  2. additionthe residue is mixed with water
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-76e6d38a56564351a0fa164bcf41d456
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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