Formic Acid → HCID 118875313, compound

HRID 60164Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH:32]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)O)=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]([CH3:31])[CH3:30])[N:21]=[CH:22][C:15]=2[N:14]([CH3:41])[C:13]1=[O:42])(C(C)(C)C)(C)C.[CH:43](O)=[O:44]>CC(=O)OCC.O.[Zn]>[CH:43]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH2:32][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]([CH3:30])[CH3:31])[N:21]=[CH:22][C:15]=2[N:14]([CH3:41])[C:13]1=[O:42])=[O:44]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(3-(tert-butyldimethylsilyloxy)propyl)-5-((4-chlorophenyl)(hydroxy)methyl)-6-(2-isopropylphenyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (15 mg, 0.0247 mmol) in HCOOH (1 mL) was added Zn dust (8 mg, 0.123 mmol). The reaction was heated at 50° C. for 1 h, cooled to RT then diluted with EA (5 mL) and water (1 mL). The organic layer was washed with brine (1 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep TLC eluted with PE/EA (2:1) to give 3-(5-(4-chlorobenzyl)-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (7 mg, 56% yield) as a colorless oil. LCMS: MH+ 506 and TR=2.225 min.

Workup

temperaturecooled to RT
washThe organic layer was washed with brine (1 mL)
dry with materialdried over Na2SO4
concentrationconcentrated to a residue which
customwas purified by Prep TLC
washeluted with PE/EA (2:1)

Sources & evidence

ORD record: ord-818f994a0ced4c8e8d93e2ded4cda3e1
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440973B2

Reaction notes

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