5-(hydroxy(phenyl)methyl)-6-isopropoxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione → 3-(5-benzyl-6-isopropoxy-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

HRID 60470Notes

Reaction equation

O[CH:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][O:17][CH:18]3CCCC[O:19]3)[C:9](=[O:24])[N:8]([CH3:25])[C:7]=2[N:6]=[CH:5][C:4]=1[O:26][CH:27]([CH3:29])[CH3:28]>C(O)=O.[Zn]>[CH:18]([O:17][CH2:16][CH2:15][CH2:14][N:10]1[C:11](=[O:13])[C:12]2[C:3]([CH2:2][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:4]([O:26][CH:27]([CH3:28])[CH3:29])[CH:5]=[N:6][C:7]=2[N:8]([CH3:25])[C:9]1=[O:24])=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-(hydroxy(phenyl)methyl)-6-isopropoxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (100 mg, 0.207 mmol) in HCOOH (2 mL) was added Zn dust (67.2 mg, 1.034 mmol). The reaction was heated at 80° C. for 1 h then cooled to RT and filtered. The filtrate was concentrated and dried to a residue which was purified by Prep TLC eluted with PE/EA (2:1) to give 3-(5-benzyl-6-isopropoxy-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (70 mg, 85% yield) as a white solid.

Workup

temperaturethen cooled to RT
filtrationfiltered
concentrationThe filtrate was concentrated
customdried to a residue which
customwas purified by Prep TLC
washeluted with PE/EA (2:1)

Sources & evidence

ORD record: ord-bd117a8ed0004d0ab02a0c19912f1d93
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440972B2

Reaction notes

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