Hydrochloric Acid → (R)-6-(2,3-Dihydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 624558Notes

Reaction equation

HRID 624558 reaction equation
Cl.CC1(C)[O:7][C@H:6]([CH2:8][N:9]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[C:16]3[C:11]([N:12]([CH3:28])[C:13](=[O:27])[N:14]([CH3:26])[C:15]3=[O:25])=[CH:10]2)[CH2:5][O:4]1.O>C(#N)C>[OH:7][C@@H:6]([CH2:5][OH:4])[CH2:8][N:9]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:16]2[C:11]([N:12]([CH3:28])[C:13](=[O:27])[N:14]([CH3:26])[C:15]2=[O:25])=[CH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86722882(R)-6-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86722881(R)-6-(2,3-Dihydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

HCl (2 M in diethyl ether) (92 ml, 185 mmol) was added dropwise to a solution of (R)-6-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 1) (7.15 g, 18.46 mmol) and water (6.65 g, 369 mmol) in acetonitrile (35.1 mL). The mixture was stirred at room temperature for 30 minutes. Evaporation of the reaction mixture under vacuum afforded the title compound.

Workup

  1. customEvaporation of the reaction mixture under vacuum

Sources & evidence

ORD record
ord-c8cc25a0d68b4749b802da745233073b
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

Loading…