Phosphorus oxychloride → HCID 86677067, compound

HRID 1520319Notes

Reaction equation

HRID 1520319 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[N:7]=[C:6]2O.O=P(Cl)(Cl)[Cl:22]>CN(C)C1C=CC=CC=1>[Cl:22][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487830HCID 178487830, compound

Product 1

HCID 86677067HCID 86677067, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineCatalyst

Conditions

Temperature
120 °C

Procedure

To a mixture of 6-methoxy-2-(pyridin-3-yl) quinazolin-4-ol (600 mg, 2.37 mmol) in POCl3 (5 mL) was added N,N-dimethyl aniline (1 drop). The resulting mixture was stirred at 120° C. for 30 min. After the reaction was completed, POCl3 was removed in vacuo, and the residue was added to ice-water slowly. The pH was adjusted to ˜7 by slowly adding NaHCO3 (sat.) at 0° C. and then a precipitate formed. The solid was collected and was purified by chromatography on silica gel eluted with petroleum ether/ethyl acetate (v/v=4:1 to 1:1) to give 260 mg of 4-chloro-6-methoxy-2-(pyridin-3-yl)quinazoline as a pale yellow solid (40.4%). LCMS m/z=272.1, 274.0 (M+1) (Method B) (retention time=1.90 min).

Workup

  1. customPOCl3 was removed in vacuo
  2. additionthe residue was added to ice-water slowly
  3. customwas adjusted to ˜7 by slowly adding NaHCO3 (sat.) at 0° C.
  4. customa precipitate formed
  5. customThe solid was collected
  6. customwas purified by chromatography on silica gel
  7. washeluted with petroleum ether/ethyl acetate (v/v=4:1 to 1:1)

Sources & evidence

ORD record
ord-03c00321e3fd412884986642290fb37b
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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