Phosphorus oxychloride → HCID 86686098, compound

HRID 1469006Notes

Reaction equation

HRID 1469006 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([N:19]2[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]2)[NH:3]1.O=P(Cl)(Cl)[Cl:31]>>[Cl:31][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([N:19]2[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136387801HCID 136387801, compound

Product 1

HCID 86686098HCID 86686098, compoundYield 77.2%

Procedure

A mixture of the above ethyl 1-(4-oxo-7-phenoxy-3,4-dihydroquinazolin-2-yl)-1H-pyrazole-4-carboxylate (0.31 g, 0.82 mmol), and POCl3 (3.08 mL, 32.9 mmol), was heated to reflux for 3 h. The mixture was allowed to cool to rt and then concentrated. The residue was taken up in a minimal amount of DCM and purified by FCC (0 to 25% EtOAc/hexanes) to yield the title compound (250 mg, 77%). 1H NMR (600 MHz, DMSO-d6): 9.06 (d, J=0.7 Hz, 1H), 8.35 (d, J=9.2 Hz, 1H), 8.23 (dd, J=10.6, 6.6 Hz, 1H), 7.63-7.59 (m, 1H), 7.60-7.54 (m, 2H), 7.41-7.36 (m, 1H), 7.31-7.29 (m, 2H), 7.18 (d, J=2.4 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 1.35-1.24 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated
  4. custompurified by FCC (0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-de1b4e78fdef41f9a59b8e7affb88a0d
Source dataset
uspto-grants-2015_04
Patent number
US09006251B2

Reaction notes

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