Lithium hydroxide, monohydrate → 3-(3-hydroxypropyl)-5-isopentyl-6-isopropoxy-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 60494Notes

Reaction equation

HRID 60494 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:15]([O:18][CH:19]([CH3:21])[CH3:20])[CH:16]=[N:17][C:10]=2[N:9]([CH3:27])[C:8]1=[O:28])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[OH:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:15]([O:18][CH:19]([CH3:21])[CH3:20])[CH:16]=[N:17][C:10]=2[N:9]([CH3:27])[C:8]1=[O:28]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118875903HCID 118875903, compound

Product 1

HCID 1188755363-(3-hydroxypropyl)-5-isopentyl-6-isopropoxy-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 50.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-isopentyl-6-isopropoxy-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (48 mg, 0.123 mmol) in THF (1 mL) and water (1 mL) was added LiOH.H2O (10.3 mg, 0.246 mmol). The reaction was stirred at RT for 15 min then diluted with EA (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 3-(3-hydroxypropyl)-5-isopentyl-6-isopropoxy-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (22.6 mg, 50.5% yield) as a white solid. 1H NMR (CDCl3) δ: 8.24 (s, 1H), 4.61-4.56 (m, 1H), 4.32-4.13 (m, 2H), 3.68 (s, 3H), 3.55 (d, J=5.3 Hz, 2H), 3.32 (dd, J=17.2, 9.1 Hz, 3H), 2.02-1.84 (m, 2H), 1.71 (dd, J=13.2, 6.6 Hz, 1H), 1.39 (d, J=6.0 Hz, 6H), 0.99 (d, J=6.6 Hz, 6H). LCMS: MH+ 364 and TR=3.032 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated to a residue which
  3. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-fa82a71cafd64f05acdf5d4f8c4491bb
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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