Lithium hydroxide, monohydrate → 5-(4-chlorobenzyl)-7-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

HRID 60366Notes

Reaction equation

HRID 60366 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[C:11]=2[N:10]([CH3:33])[C:9]1=[O:34])(=O)C.O[Li].O>C1COCC1.O.CC(=O)OCC>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:15]2[C:12]3[C:13](=[O:14])[N:8]([CH2:7][CH2:6][CH2:5][OH:4])[C:9](=[O:34])[N:10]([CH3:33])[C:11]=3[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[CH:16]2)=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118863778HCID 118863778, compound

Product 1

HCID 1188637895-(4-chlorobenzyl)-7-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dioneYield 43.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-7-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (50 mg, 0.1 mmol) in THF (0.5 mL) and water (0.5 mL) was added LiOH.H2O (8.4 mg, 0.2 mmol). The reaction was stirred at RT for 30 min 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)-7-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (20 mg, 41% yield). 1H NMR (CDCl3) δ: 7.39-7.29 (m, 5H), 7.25-7.17 (m, 3H), 6.91 (s, 1H), 5.56 (s, 2H), 4.28-4.15 (m, 2H), 3.62 (s, 1H), 3.52 (d, J=4.8 Hz, 2H), 3.21 (s, 3H), 1.96-1.82 (m, 2H). LCMS: MH+ 458 and TR=2.953 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-3563b148b1a5441798f0aba5df5387c2
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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