Lithium hydroxide, monohydrate → HCID 118875489, compound

HRID 60464Notes

Reaction equation

HRID 60464 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:15]([O:18][C:19]3[CH:20]=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=3)[CH:16]=[N:17][C:10]=2[N:9]([CH3:34])[C:8]1=[O:35])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C:14]2[C:11]3[C:12](=[O:13])[N:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:8](=[O:35])[N:9]([CH3:34])[C:10]=3[N:17]=[CH:16][C:15]=2[O:18][C:19]2[CH:20]=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118875893HCID 118875893, compound

Product 1

HCID 118875489HCID 118875489, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-6-(5-methylpyridin-3-yloxy)-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (56 mg, 0.113 mmol) in THF (3 mL) and water (3 mL) was added LiOH.H2O (9.5 mg, 0.226 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 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1-methyl-6-(5-methylpyridin-3-yloxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (11 mg, 21% yield) as a white solid. 1H NMR (CD3OD) δ: 8.43 (s, 1H), 8.13-7.95 (m, 2H), 7.22-7.05 (m, 4H), 6.94 (s, 1H), 4.81 (s, 2H), 4.18 (t, J=7.1 Hz, 2H), 3.72 (s, 3H), 3.65 (t, J=6.3 Hz, 2H), 2.24 (s, 3H), 1.98-1.84 (m, 2H). LCMS: MH+ 467 and TR=2.631 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-3779db9e13f34c5484cd33c21b6a6735
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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