Lithium hydroxide, monohydrate → HCID 118874983, compound

HRID 60156Notes

Reaction equation

HRID 60156 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]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:16]=[CH: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[CH:17]=[N:16][C:15]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1188753123-(5-(4-chlorobenzyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

Product 1

HCID 118874983HCID 118874983, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (16 mg, 0.032 mmol) in THF (0.5 mL) and H2O (0.5 mL) was added LiOH.H2O (2.7 mg, 0.064 mmol). The reaction was stirred at RT for 0.5 h then diluted with EA (5 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(4-chlorophenyl)-3-(3-hydroxypropyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (6 mg, 80%) as a white solid. 1H NMR (CDCl3) δ: 8.79 (s, 1H), 7.42-7.33 (m, 2H), 7.28 (d, J=1.9 Hz, 1H), 7.26 (s, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.80 (d, J=8.4 Hz, 2H), 4.64 (s, 2H), 4.17 (t, J=6.2 Hz, 2H), 3.74 (s, 3H), 3.46 (dd, J=11.5, 5.9 Hz, 2H), 2.70 (t, J=6.7 Hz, 1H), 1.96-1.71 (m, 2H). LCMS: MH+ 470 and TR=2.924 min.

Workup

  1. washThe organic layer was washed with brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to a residue which
  4. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-3e021879690547b2ab66de00ea6ab28c
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

Loading…