2,6-Lutidine → HCID 22030341, compound

HRID 968626Notes

Reaction equation

HRID 968626 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[C:4]([C:9]2[CH:18]=[N:17][C:16]3[C:15](=O)[NH:14][C:13]([CH2:20][O:21][CH3:22])=[N:12][C:11]=3[CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.N1C(C)=CC=CC=1C.P(Cl)(Cl)([Cl:35])=O>C(Cl)(Cl)Cl>[Cl:35][C:15]1[C:16]2[N:17]=[CH:18][C:9]([C:4]3[C:3]([C:2]([F:24])([F:23])[F:1])=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:10][C:11]=2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 135682064HCID 135682064, compound

Product 1

HCID 22030341HCID 22030341, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 7-(3-trifluoromethyl-pyridin-2-yl)-2-methoxymethyl-3H-pyrido[3,2-d]pyrimidin-4-one (276 mg, 0.822 mmol) in CHCl3 (25 mL) and 2,6-lutidine (294 mg, 2.74 mmol). Add phosphorous oxycloride (0.255 mL, 2.74 mmol) dropwise and heat the resulting solution to reflux for 24 hours. Cool the solution and remove the solvent under reduced pressure. Partition the crude residue between EtOAc (50 mL) and saturated NaHCO3 (aq) (50 mL). Remove the organic phase and extract the aqueous phase with additional EtOAc (50 mL). Combine the two organic extracts, wash with brine (100 mL), and dry over Na2SO4. Remove the solvent to yield the title compound as a light brown solid.

Workup

  1. temperatureto reflux for 24 hours
  2. temperatureCool the solution
  3. customremove the solvent under reduced pressure
  4. customPartition the crude residue between EtOAc (50 mL) and saturated NaHCO3 (aq) (50 mL)
  5. customRemove the organic phase
  6. extractionextract the aqueous phase with additional EtOAc (50 mL)
  7. washCombine the two organic extracts, wash with brine (100 mL)
  8. dry with materialdry over Na2SO4
  9. customRemove the solvent

Sources & evidence

ORD record
ord-0b1c0c215e0a40efbeb801db3dfb83a9
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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