Lithium hydroxide, monohydrate → HCID 118875521, compound

HRID 60502Notes

Reaction equation

HRID 60502 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH:25]([CH3:27])[CH3:26])[CH:16]=[N:17][C:10]=2[N:9]([CH3:36])[C:8]1=[O:37])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[F:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][C:14]2[C:11]3[C:12](=[O:13])[N:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:8](=[O:37])[N:9]([CH3:36])[C:10]=3[N:17]=[CH:16][C:15]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH:25]([CH3:26])[CH3:27])=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118875465HCID 118875465, compound

Product 1

HCID 118875521HCID 118875521, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-fluorobenzyl)-6-(2-isopropylphenoxy)-1-methyl-2,4-dioxo-1,2-dihydro pyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (68 mg, 0.135 mmol) in THF (1 ml) and water (1 mL) was added LiOH.H2O (14 mg, 0.33 mmol). The reaction was stirred at RT for 15 min then diluted with EA (10 mL) and water (10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-fluorobenzyl)-3-(3-hydroxypropyl)-6-(2-isopropylphenoxy)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (55 mg, 85.4% yield) as a white solid. 1H NMR (DMSO-d6) δ: 8.23 (s, 1H), 7.38-7.35 (m, 1H), 7.23-7.18 (m, 2H), 7.14-7.10 (m, 2H), 7.03 (t, J=8.8 Hz, 2H), 6.61-6.58 (m, 1H), 4.71 (s, 2H), 4.49 (t, J=5.2 Hz, 1H), 3.98 (t, J=7.2 Hz, 2H), 3.56 (s, 3H), 3.49-3.43 (m, 2H), 3.11-3.07 (m, 1H), 1.75-1.71 (m, 2H), 1.12 (d, J=6.4 Hz, 6H). LCMS: MH+ 478 and TR=3.356 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-bbbb1a7ac02348be9e5598d41b684295
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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