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

HRID 60456Notes

Reaction equation

HRID 60456 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])[CH:16]=[N:17][C:10]=2[N:9]([CH3:32])[C:8]1=[O:33])=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]([CH2:27][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])[CH:16]=[N:17][C:10]=2[N:9]([CH3:32])[C:8]1=[O:33]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1188759083-(5-isopentyl-6-(2-isopropyl phenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformate

Product 1

HCID 1188754843-(3-hydroxypropyl)-5-isopentyl-6-(2-isopropylphenyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 57.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-isopentyl-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (15 mg, 0.033 mmol) in THF (4 mL) and water (4 mL) was added LiOH.H2O (2.79 mg, 0.066 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 chromatography eluted with PE/EA (10:1) to give 3-(3-hydroxypropyl)-5-isopentyl-6-(2-isopropylphenyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (8 mg, 56.8% yield) as a white solid. 1H NMR (CDCl3) δ: 8.35 (s, 1H), 7.43-7.42 (d, J=4.0 Hz, 2H), 7.28-7.24 (m, 1H), 7.07-7.05 (m, 1H), 4.27 (m, 3H), 3.76 (s, 3H), 3.58 (s, 2H), 3.40-3.31 (m, 2H), 2.68-2.54 (m, 2H), 1.97-1.94 (m, 2H), 1.57 (m, 1H), 1.22-1.19 (m, 3H), 1.08-1.06 (m, 3H), 0.71-0.69 (m, 3H), 0.64-0.62 (d, J=8 Hz, 3H). LCMS: MH+ 424 and TR=3.546 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated to a residue which
  3. customwas purified by chromatography
  4. washeluted with PE/EA (10:1)

Sources & evidence

ORD record
ord-d87e7f9b32724f4587bc50b98a1a6234
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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