5-Phenyl-1-pentanol → HCID 135899209, compound

HRID 2100516Notes

Reaction equation

HRID 2100516 reaction equation
Cl.Cl[C:3]1[NH:4][C:5](=[O:14])[C:6]2[C:12]([CH3:13])=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1.[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC([O-])(C)C.[K+]>CS(C)=O>[CH3:13][C:12]1[C:6]2[C:5](=[O:14])[NH:4][C:3]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:8][C:7]=2[N:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 615235-Phenyl-1-pentanolHCID 23665647Potassium tert-butoxideHCID 136345786HCID 136345786, compound

Product 1

HCID 135899209HCID 135899209, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-5-methyl-3H-pyrido[2,3-d]pyrimidin-4-one hydrochloride (36 mg, 155 μmol) was dissolved in DMSO (0.8 ml). Molecular sieves 4Å, 5-phenyl-1-pentanol (80 μl, 465 μmmol) and potassium tert-butylate (35 mg, 310 μmol) were added and the suspension was stirred at 120° C. for 48 h under an argon atmosphere. The molecular sieves were filtered off, the filtrate was poured onto ice water/isopropyl acetate 1/1, the layers were separated and the aqueous layer was extracted two times with isopropyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, isopropyl acetate/heptane) to give 5-methyl-2-(5-phenyl-pentyloxy)-3H-pyrido[2,3-d]pyrimidin-4-one (16 mg, 50 μmol; 32%) as yellow crystals. MS: m/e=324.4 [M+H+].

Workup

  1. additionwere added
  2. filtrationThe molecular sieves were filtered off
  3. additionthe filtrate was poured onto ice water/isopropyl acetate 1/1
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted two times with isopropyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe crude product was purified by column chromatography (silica gel, isopropyl acetate/heptane)

Sources & evidence

ORD record
ord-ba15645d65eb4049b3e0d587993f8161
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

Loading…