Lithium hydroxide, monohydrate → HCID 118875495, compound

HRID 60421Notes

Reaction equation

HRID 60421 reaction equation
C([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[C:14]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[C:15]([O:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[N:17][C:10]=2[N:9]([CH3:33])[C:8]1=[O:34])=O.O[Li].O>C1COCC1.O.CC(=O)OCC>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][C:14]2[C:11]3[C:12](=[O:13])[N:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:8](=[O:34])[N:9]([CH3:33])[C:10]=3[N:17]=[CH:16][C:15]=2[O:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1188759093-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(pyridin-3-yloxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

Product 1

HCID 118875495HCID 118875495, compoundYield 63.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(pyridin-3-yloxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (10.3 mg, 0.021 mmol) in THF (5 mL) and water (5 mL), was added LiOH.H2O (1.80 mg, 0.042 mmol) The reaction was stirred at RT for 30 min then diluted with EA (10 mL) and water (10 mL). The organic layer was dried over Na2SO4, filtered and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1-methyl-6-(pyridin-3-yloxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6 mg, 61.8% yield) as a white solid. 1H NMR (CDCl3) δ: 8.39 (d, J=4.6 Hz, 1H), 8.33 (d, J=4.5 Hz, 2H), 7.24 (d, J=4.7 Hz, 1H), 7.17 (s, 4H), 7.10 (dd, J=8.4, 1.6 Hz, 1H), 4.75 (s, 2H), 4.24 (t, J=6.1 Hz, 2H), 3.71 (s, 3H), 3.62-3.49 (m, 2H), 2.99 (t, J=6.8 Hz, 1H), 2.00-1.84 (m, 2H). LCMS: MH+ 453 and TR=1.963 min.

Workup

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

Sources & evidence

ORD record
ord-17b68057470046ba952c7515542c5af3
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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