Water → HCID 118875025, compound

HRID 60167Notes

Reaction equation

HRID 60167 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([CH3:26])[CH3:25])[N:16]=[CH:17][C:10]=2[N:9]([CH3:32])[C:8]1=[O:33])=O.O.O[Li].O>C1COCC1.CC(=O)OCC>[OH:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([CH3:26])[CH3:25])[N:16]=[CH:17][C:10]=2[N:9]([CH3:32])[C:8]1=[O:33]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 1188753153-(5-isopentyl-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

Product 1

HCID 118875025HCID 118875025, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-isopentyl-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (10 mg, 0.022 mmol in THF (0.5 mL) and water (0.5 mL) was added LiOH.H2O (1.8 mg, 0.044 mmol). The reaction was stirred at RT for 30 min then diluted with EA (5 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 3-(3-hydroxypropyl)-5-isopentyl-6-(2-isopropylphenyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (2.2 mg, 23.6% yield) as a white solid. 1H NMR (CDCl3) δ: 8.66 (s, 1H), 7.41 (d, J=3.8 Hz, 2H), 7.26-7.23 (m, 1H), 7.11 (d, J=7.5 Hz, 1H), 4.28 (t, J=6.1 Hz, 2H), 3.72 (s, 3H), 3.65-3.54 (m, 2H), 3.35 (td, J=11.8, 4.5 Hz, 1H), 3.14 (t, J=6.6 Hz, 1H), 2.69 (d, J=11.9, 4.4 Hz, 1H), 2.53-2.40 (m, 1H), 2.04-1.91 (m, 2H), 1.45 (d, J=12.9, 6.4 Hz, 1H), 1.38-1.32 (m, 1H), 1.19 (d, J=6.9 Hz, 3H), 1.14 (dd, J=7.1, 4.8 Hz, 1H), 1.10 (d, J=6.8 Hz, 3H), 0.72 (d, J=6.6 Hz, 3H), 0.65 (d, J=6.6 Hz, 3H). LCMS: MH+ 424 and TR=3.102 min.

Workup

  1. washThe organic layer was washed with brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to a residue which
  4. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-5d67a79782224ecea6df99f63d8ebd03
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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