Lithium hydroxide, monohydrate → HCID 118875502, compound

HRID 60468Notes

Reaction equation

HRID 60468 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][CH:32]=[CH:31][CH:30]=3)=[C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:20]=3)[CH:16]=[N:17][C:10]=2[N:9]([CH3:35])[C:8]1=[O:36])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[CH2:28]([C:14]1[C:11]2[C:12](=[O:13])[N:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:8](=[O:36])[N:9]([CH3:35])[C:10]=2[N:17]=[CH:16][C:15]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:20]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118875475HCID 118875475, compound

Product 1

HCID 118875502HCID 118875502, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-benzyl-6-(3-isopropylphenoxy)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (50 mg, 0.10 mmol) in THF (3 ml) and water (3 mL) was added LiOH.H2O (10 mg, 0.20 mmol). The reaction was stirred at RT for 15 min then diluted with EA (30 mL) and water (30 mL). The organic layer was dried over Na2SO4 and concentrated to give a residue which was purified by Prep HPLC to give 5-benzyl-3-(3-hydroxypropyl)-6-(3-isopropyl phenoxy)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (15 mg, 45% yield) as a solid. 1H NMR (CDCl3) δ: 8.32 (s, 1H), 7.29 (s, 2H), 7.25-7.12 (m, 4H), 6.99 (d, J=7.9 Hz, 1H), 6.76 (s, 1H), 6.68 (dd, J=8.0, 2.3 Hz, 1H), 4.80 (s, 2H), 4.24 (t, J=6.0 Hz, 2H), 3.70 (s, 3H), 3.52 (dd, J=11.8, 6.2 Hz, 2H), 3.10 (t, J=7.0 Hz, 1H), 2.85 (dt, J=13.9, 6.9 Hz, 1H), 1.98-1.83 (m, 2H), 1.22 (d, J=6.9 Hz, 6H). LCMS: MH+ 460 and TR=3.376 min.

Workup

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

Sources & evidence

ORD record
ord-f6d6ca5196c74a809c3463f4e18c3cc2
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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