Methanol → 8-(6-Acetyl-4-ethoxy-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-5-yl)-2-methyl-4H-chromen-4-one

HRID 1947250Notes

Reaction equation

HRID 1947250 reaction equation
[C:1]([C:4]1[CH:5]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[O:24][C:23]([CH3:26])=[CH:22][C:21]3=[O:27])[C:6]2[C:11](=[O:12])[NH:10][CH:9]=[N:8][C:7]=2[NH:13][C:14]=1[CH3:15])(=[O:3])[CH3:2].F[B-](F)(F)F.[CH2:33]([O+](CC)CC)[CH3:34].CO>ClCCl>[C:1]([C:4]1[CH:5]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[O:24][C:23]([CH3:26])=[CH:22][C:21]3=[O:27])[C:6]2[C:11]([O:12][CH2:33][CH3:34])=[N:10][CH:9]=[N:8][C:7]=2[NH:13][C:14]=1[CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 2723982Triethyloxonium tetrafluoroborateHCID 1361308496-Acetyl-7-methyl-5-(2-methyl-4-oxo-4H-chromen-8-yl)-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 236279908-(6-Acetyl-4-ethoxy-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-5-yl)-2-methyl-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

140 mg (0.38 mmol) of 6-acetyl-7-methyl-5-(2-methyl-4-oxo-4H-chromen-8-yl)-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one are suspended under an argon atmosphere in dichloromethane (7 ml), 219 mg (1.15 mmol) of triethyloxonium tetrafluoroborate are added, and the mixture is stirred at RT for 12 h. The reaction mixture is then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 9 mg (6% of theory) of the title compound are obtained as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-66b20ada06bd4533b5f7e3c2bd041e20
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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