HCID 68679872, compound → HCID 59128647, compound

HRID 1991014Notes

Reaction equation

HRID 1991014 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:23])=[C:7]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=2)[CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH3:23][C:6]1[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][C:7]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

4

Reactant 1

HCID 68679872HCID 68679872, compound

Product 1

HCID 59128647HCID 59128647, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

6-(5-Hydroxymethyl-2-methyl-phenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (129 mg, 0.394 mmol) was dissolved in 7 mL methylene chloride at room temperature, and MnO2 (343 mg, 3.94 mmol) was added. The reaction mixture was stirred for 48 hours at room temperature, then filtered through Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by preparative TLC plate, eluting with 5% MeOH/DCM, to give 73 mg of 4-methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzaldehyde, MS (M+H)=326.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by preparative TLC plate
  4. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-d991401276644cf5996c9c4cd77511bc
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

Loading…