Lithium hydroxide, monohydrate → HCID 118875317, compound

HRID 60159Notes

Reaction equation

HRID 60159 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:16]=[CH:17][C:10]=2[N:9]([CH3:30])[C:8]1=[O:31])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[N:16]=[CH:17][C:10]3[N:9]([CH3:30])[C:8](=[O:31])[N:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:12](=[O:13])[C:11]=3[C:14]=2[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1188753113-(6-(4-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

Product 1

HCID 118875317HCID 118875317, compoundYield 57.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(6-(4-chlorophenyl)-5-isopentyl-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (13 mg, 0.029 mmol) in THF (0.5 mL) and H2O (0.5 mL) was added LiOH.H2O (2.46 mg, 0.058 mmol). The reaction was stirred at RT for 30 min then diluted with EA (5 mL). The organic layer was washed with brine (1 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 6-(4-chlorophenyl)-3-(3-hydroxypropyl)-5-isopentyl-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (6.9 mg, 57% yield) as a white solid. 1H NMR (CDCl3) δ: 8.65 (s, 1H), 7.49-7.41 (m, 2H), 7.38-7.31 (m, 2H), 4.28 (t, J=6.1 Hz, 2H), 3.71 (s, 3H), 3.64-3.53 (m, 2H), 3.27-3.13 (m, 2H), 3.07 (t, J=6.9 Hz, 1H), 2.02-1.90 (m, 2H), 1.53 (dd, J=13.2, 6.6 Hz, 1H), 1.31 (dd, J=16.3, 6.7 Hz, 2H), 0.78 (d, J=6.6 Hz, 6H). LCMS: MH+ 416 and TR=3.048 min.

Workup

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

Sources & evidence

ORD record
ord-abae8fbba5be40019e653699d97a68ab
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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