Phosphorus oxychloride → HCID 20092843, compound

HRID 274254Notes

Reaction equation

HRID 274254 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:17]([CH2:26][CH2:27][CH3:28])=[N:18][C:19]3[N:20]([N:23]=[CH:24][CH:25]=3)[C:21]=2O)=[CH:11][CH:10]=1)#[N:2].O=P(Cl)(Cl)[Cl:31]>ClCCl>[Cl:31][C:21]1[N:20]2[N:23]=[CH:24][CH:25]=[C:19]2[N:18]=[C:17]([CH2:26][CH2:27][CH3:28])[C:16]=1[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178439969HCID 178439969, compound

Product 1

HCID 20092843HCID 20092843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27 g of 6-[(2'-cyanobiphenyl-4-yl)methyl]-7-hydroxy-5-propylpyrazolo[1,5-a]pyrimidine, prepared in Example 18, are added in portions to 540 ml of POCl3. The mixture is refluxed for 3 h. It is concentrated under vacuum. The oil obtained is taken up in dichloromethane and washed twice with a solution of water and ice. The organic phase is decanted, dried and concentrated. The yellow oil is taken up in ether to give 25.6 g of crystals of 7-chloro-6-[(2'-cyanobiphenyl-4-yl)methyl]-5-propylpyrazolo[1,5-a]pyrimidine.

Workup

  1. temperatureThe mixture is refluxed for 3 h
  2. concentrationIt is concentrated under vacuum
  3. customThe oil obtained
  4. washwashed twice with a solution of water and ice
  5. customThe organic phase is decanted
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3459d4e14ebb426aa4acf787735008eb
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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