HCID 118874980, compound → 3-(6-(4-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

HRID 60173Notes

Reaction equation

HRID 60173 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20](Cl)[CH:19]=3)[N:16]=[CH:17][C:10]=2[N:9]([CH3:30])[C:8]1=[O:31])=[O:2].C(OCCCN1C(=O)C2C(CCC(C)C)=C(C3C=CC=C([Cl:55])C=3)NCC=2N(C)C1=O)=O>C(Cl)Cl.O.O=[Mn]=O>[CH:1]([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:55])=[CH:20][CH:19]=3)[N:16]=[CH:17][C:10]=2[N:9]([CH3:30])[C:8]1=[O:31])=[O:2]

Participants

6

Reactant 2

HCID 118874980HCID 118874980, compoundHCID 118874985HCID 118874985, compound

Product 1

HCID 1188753113-(6-(4-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formateYield 66.7%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(6-(3-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate and 3-(6-(3-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2,7,8-tetrahydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (21 mg, 0.047 mmol) in DCM (1 mL) was added MnO2 (40.8 mg, 0.47 mmol). The reaction was stirred at RT for 3 h then diluted with DCM (5 mL) and water (1 mL). The organic layer was washed with brine (1 mL), dried over Na2SO4, and concentrated to give 3-(6-(4-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (14 mg, 66.7% yield) as an oil. LCMS: MH+ 444 and TR=1.942 min. Used without further purification.

Workup

  1. washThe organic layer was washed with brine (1 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0474dd6e1629483c92688c593d790200
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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