Formic Acid → HCID 118874985, compound

HRID 60172Notes

Reaction equation

HRID 60172 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH:30](O)[CH2:31][CH:32]([CH3:34])[CH3:33])=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[N:21]=[CH:22][C:15]=2[N:14]([CH3:36])[C:13]1=[O:37])(C(C)(C)C)(C)C.[CH:38](O)=[O:39]>CC(=O)OCC.O.[Zn]>[CH:38]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[N:21]=[CH:22][C:15]=2[N:14]([CH3:36])[C:13]1=[O:37])=[O:39]

Participants

6

Reactant 2

HCID 284Formic AcidHCID 131737086HCID 131737086, compound

Product 1

HCID 118874985HCID 118874985, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(3-(tert-butyldimethylsilyloxy)propyl)-6-(3-chlorophenyl)-5-(1-hydroxy-3-methylbutyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (30 mg, 0.055 mmol) in HCOOH (1 mL) was added Zn dust (35.6 mg, 0.55 mmol). The reaction was heated at 50° C. for 1 h, cooled to RT and diluted with EA (5 mL) and water (1 mL). The organic layer was washed with brine (1 mL), dried over Na2SO4 and concentrated to give 3-(6-(3-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate. LCMS MH+ 444 and TR=1.738 min 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. LCMS: MH+ 446 and TR=1.956 min, (21 mg, 70% yield) as a solid. Used without further purification.

Workup

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

Sources & evidence

ORD record
ord-d198113b6a7a42619be574a4c12b48c3
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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