Phosphorus oxychloride → HCID 86664778, compound

HRID 2047006Notes

Reaction equation

HRID 2047006 reaction equation
O[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:13][CH2:12]2)[CH:3]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:42]>>[Cl:42][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:13][CH2:12]2)[CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178450660HCID 178450660, compound

Product 1

HCID 86664778HCID 86664778, compound

Procedure

Di-tert-butyl 5-(7-hydroxypyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1,2-dicarboxylate (16.7 mmol, 7.0 g), N,N′-diisopropylethylamine (51.9 mmol, 9.0 ml) and POCl3 (80 mL) were mixed and stirred at room temperature for 18 hours. The solution is concentrated in vacuo and cooled to 0° C. in an ice bath. The reaction is then quenched with sat. NaHCO3(aq) and extracted with DCM (100 mL×3). The combined organics are dried with Na2SO4 and the solvent removed in vacuo. LC-MS: 437 [M+H]. The resulting oil was used in the next step without further purification.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. temperaturecooled to 0° C. in an ice bath
  3. customThe reaction is then quenched with sat. NaHCO3(aq)
  4. extractionextracted with DCM (100 mL×3)
  5. dry with materialThe combined organics are dried with Na2SO4
  6. customthe solvent removed in vacuo
  7. customThe resulting oil was used in the next step without further purification

Sources & evidence

ORD record
ord-7fdc4e0a12b643069b43d738175fc12b
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…