Lithium hydroxide, monohydrate → HCID 118874989, compound

HRID 60178Notes

Reaction equation

HRID 60178 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=3)[N:16]=[CH:17][C:10]=2[N:9]([CH3:36])[C:8]1=[O:37])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[CH2:29]([C:14]1[C:11]2[C:12](=[O:13])[N:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:8](=[O:37])[N:9]([CH3:36])[C:10]=2[CH:17]=[N:16][C:15]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1188753103-(5-benzyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydro pyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

Product 1

HCID 118874989HCID 118874989, compoundYield 56.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-benzyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydro pyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (50 mg, 0.097 mmol) in THF (0.5 mL) and water (0.5 mL) was added LiOH.H2O (8.18 mg, 0.194 mmol). The reaction was stirred at RT for 30 min then diluted with EA (5 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-benzyl-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenyl)pyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (26.4 mg, 56% yield) as a white solid. 1H NMR (CDCl3) δ: 8.79 (s, 1H), 7.45-7.37 (m, 1H), 7.29 (d, J=7.7 Hz, 1H), 7.24 (s, 2H), 7.22-7.11 (m, 3H), 6.86 (d, J=7.1 Hz, 2H), 4.71 (s, 2H), 4.18 (t, J=6.1 Hz, 2H), 3.73 (d, J=13.2 Hz, 3H), 3.42 (t, J=5.6 Hz, 2H), 1.88-1.76 (m, 2H). LCMS: MH+ 486 and TR=2.808 min

Workup

  1. washThe organic layer was washed with brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to a residue which
  4. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-e16bedeb84c1400298c1f94e35c1f3b5
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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