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

HRID 60359Notes

Reaction equation

HRID 60359 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH:16]=[C:17]([CH3:18])[C:11]=2[N:10]([CH3:27])[C:9]1=[O:28])(=O)C.O[Li].O>C1COCC1.O.C(Cl)Cl>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:15]2[C:12]3[C:13](=[O:14])[N:8]([CH2:7][CH2:6][CH2:5][OH:4])[C:9](=[O:28])[N:10]([CH3:27])[C:11]=3[C:17]([CH3:18])=[CH:16]2)=[CH:25][CH:24]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1188637913-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3 (2H,4H,5H)-yl)propyl acetate

Product 1

HCID 1188637735-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1,7-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dioneYield 41.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3 (2H,4H,5H)-yl)propyl acetate (40 mg, 0.099 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (4.74 mg, 0.198 mmol). The reaction was stirred at RT for 30 min then diluted with DCM (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)-1,7-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (15 mg, 41.9% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.38 (d, J=8.4 Hz, 2H), 7.26 (s, 1H), 7.22 (d, J=8.4 Hz, 2H), 5.45 (s, 2H), 4.44 (t, J=5.3 Hz, 1H), 3.95-3.82 (m, 2H), 3.56 (s, 3H), 3.45-3.39 (m, 2H), 2.26 (s, 3H), 1.73-1.58 (m, 2H). LCMS: MH+ 362 and TR=2.343 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-3e23431cfe9243f28e9dd6bf2f7f4fc7
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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