Phosphorus oxychloride → HCID 86078322, compound

HRID 2354131Notes

Reaction equation

HRID 2354131 reaction equation
O[C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:5]2[CH:10]=[N:9][C:8]([C:11]#[N:12])=[N:7][C:6]=2[N:13]=1.O=P(Cl)(Cl)[Cl:22]>CC#N>[Cl:22][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:5]2[CH:10]=[N:9][C:8]([C:11]#[N:12])=[N:7][C:6]=2[N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785105627-Hydroxy-6-phenylpyrido[2,3-d]pyrimidine-2-carbonitrile

Product 1

HCID 86078322HCID 86078322, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The solution of 7-hydroxy-6-phenylpyrido[2,3-d]pyrimidine-2-carbonitrile (2-3; 0.300 g, 1.21 mmol) in CH3CN and POCl3 (2 mL) was heated to 100° C. for 4 h. The mixture was concentrated and the residue was basified with saturated NaHCO3 at 0° C. Extracted with CH2Cl2 and the combined organic layer was dried, filtered and concentrated. The residue was purified by silica gel chromatography (10-20% EtOAc in hexane) to give the title compound (2-4). LRMS m/z (M+H) Calcd: 267.7, found: 267.2.

Workup

  1. concentrationThe mixture was concentrated
  2. customwas basified with saturated NaHCO3 at 0° C
  3. extractionExtracted with CH2Cl2
  4. customthe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (10-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-ab10b6f779ef48f69425042a9591ac72
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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