5-(1-hydroxy-3-methylbutyl)-6-isopropoxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione → HCID 118875903, compound

HRID 60493Notes

Reaction equation

HRID 60493 reaction equation
O[CH:2]([C:7]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][O:21][CH:22]3CCCC[O:23]3)[C:13](=[O:28])[N:12]([CH3:29])[C:11]=2[N:10]=[CH:9][C:8]=1[O:30][CH:31]([CH3:33])[CH3:32])[CH2:3][CH:4]([CH3:6])[CH3:5]>C(O)=O.[Zn]>[CH:22]([O:21][CH2:20][CH2:19][CH2:18][N:14]1[C:15](=[O:17])[C:16]2[C:7]([CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[C:8]([O:30][CH:31]([CH3:33])[CH3:32])[CH:9]=[N:10][C:11]=2[N:12]([CH3:29])[C:13]1=[O:28])=[O:23]

Participants

4

Reactant 1

HCID 1188755445-(1-hydroxy-3-methylbutyl)-6-isopropoxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 118875903HCID 118875903, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(1-hydroxy-3-methylbutyl)-6-isopropoxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (60 mg, 0.13 mmol) in HCOOH (2 mL) was added Zn dust (42 mg, 0.65 mmol). The reaction was heated at 80° C. for 1 h, 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-isopentyl-6-isopropoxy-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (48 mg, 82.7% yield) as a white solid. LCMS: MH+ 392 and TR=2.964 min.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customdried to a residue which
  5. customwas purified by Prep TLC
  6. washeluted with PE/EA (2:1)

Sources & evidence

ORD record
ord-e2250f4e4a344f9993fe2ef6189dd0dd
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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