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

HRID 1805970Notes

Reaction equation

HRID 1805970 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[N:14]=[C:15](O)[C:16]4[S:21][CH2:20][CH2:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:15]1[C:16]2[S:21][CH2:20][CH2:19][C:17]=2[N:18]=[C:13]([N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517891HCID 178517891, compound

Product 1

HCID 866162644-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidineYield 100%

Conditions

Temperature
120 °C

Procedure

4.3 g (13.7 mmol) of 2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (IV) and 25 mL of phosphorus oxychloride are combined and stirred for 5 hours at 120° C. Excess phosphorus oxychloride is concentrated by evaporation, the residue is combined with ice water and dichloromethane. The organic phase is separated off and evaporated to dryness. The residue is triturated with water, suction filtered, and dried. 5.6 g of the product (100%) is obtained as a powder.

Workup

  1. concentrationExcess phosphorus oxychloride is concentrated by evaporation
  2. customThe organic phase is separated off
  3. customevaporated to dryness
  4. customThe residue is triturated with water, suction
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-332fd9c00d1f4b0ba2dadf56ced288e1
Source dataset
uspto-grants-2013_01
Patent number
US08354531B2

Reaction notes

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