Lithium hydroxide, monohydrate → 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

HRID 60349Notes

Reaction equation

HRID 60349 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)[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[CH:17][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[CH:17]=[C:16]2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118863766HCID 118863766, compound

Product 1

HCID 1188637755-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dioneYield 8.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (40 mg, 0.08 mmol) in THF (1.5 mL) and water (1.5 mL) was added LiOH.H2O (30.0 mg, 0.6 mmol). The reaction was stirred at RT for 30 min diluted with EA (10 mL) and water (10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (3 mg, 3.3% yield) as a white solid. 1H NMR (CDCl3) δ: 7.47-7.31 (m, 3H), 7.24-7.15 (m, 3H), 6.84 (d, J=8.4 Hz, 2H), 6.08 (s, 1H), 5.58 (s, 2H), 4.26-4.14 (m, 2H), 3.60 (s, 1H), 3.51 (s, 5H), 1.93-1.82 (m, 2H). LCMS: MH+ 458 and TR=2.885 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-d8cc014db4b441b19a8b8f5d6333ad5b
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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