2,6-Lutidine → HCID 22030256, compound

HRID 2054327Notes

Reaction equation

HRID 2054327 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:9]=[CH:10][C:11]3[C:16](=O)[NH:15][C:14]([CH2:18][O:19][CH3:20])=[N:13][C:12]=3[N:21]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.N1C(C)=CC=CC=1C.O=P(Cl)(Cl)[Cl:32]>C(Cl)(Cl)Cl>[Cl:32][C:16]1[C:11]2[CH:10]=[CH:9][C:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[N:21][C:12]=2[N:13]=[C:14]([CH2:18][O:19][CH3:20])[N:15]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 135682056HCID 135682056, compound

Product 1

HCID 22030256HCID 22030256, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Reflux a mixture of 7-(3-chloro-pyridin-2-yl)-2-methoxymethyl-3H-pyrido[2,3-d]pyrimidin-4-one (0.25 g), 2,6-lutidine (0.44 g), and POCl3 (0.51 g) in CHCl3 (5 mL) for 20 hours. Cool the mixture and concentrate under reduced pressure. Partition the residue between EtOAc and saturated NaHCO3 solution. Wash the EtOAc portion with additional NaHCO3 and then dry (Na2SO4) and concentrate under reduced pressure. Filter the brown residue through 2 inches of silica gel (1:1 EtOAc/hexanes eluent) and concentrate under reduced pressure to give 4-chloro-7-(3-chloro-pyridin-2-yl)-2-methoxymethyl-pyrido[2,3-d]pyrimidine.

Workup

  1. temperatureReflux
  2. temperatureCool the mixture
  3. concentrationconcentrate under reduced pressure
  4. customPartition the residue between EtOAc and saturated NaHCO3 solution
  5. washWash the EtOAc portion with additional NaHCO3
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate under reduced pressure
  8. filtrationFilter the brown residue through 2 inches of silica gel (1:1 EtOAc/hexanes eluent)
  9. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-2a5528ae069d42e4916f15458b01ee90
Source dataset
uspto-grants-2008_02
Patent number
US07329664B2

Reaction notes

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