Hydrochloric Acid → HCID 59309955, compound

HRID 1513062Notes

Reaction equation

HRID 1513062 reaction equation
[Cl:1][C:2]1[C:7](OC=C=O)=[C:6](OC)[C:5]([O:14][CH2:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]([F:24])[C:17]=2[F:25])=[CH:4][C:3]=1[N:26]1[C:34](=[O:35])[NH:33][C:32]2[C:27]1=[N:28][C:29]([CH3:38])=[N:30][C:31]=2[O:36][CH3:37].[O:39]1[CH2:43][CH2:42]CC1.[BH4-].[Na+].Cl.C([OH:49])C>>[Cl:1][C:2]1[CH:7]=[C:6]([O:49][CH2:42][CH2:43][OH:39])[C:5]([O:14][CH2:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]([F:24])[C:17]=2[F:25])=[CH:4][C:3]=1[N:26]1[C:34](=[O:35])[NH:33][C:32]2[C:27]1=[N:28][C:29]([CH3:38])=[N:30][C:31]=2[O:36][CH3:37]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86641285HCID 86641285, compound

Product 1

HCID 59309955HCID 59309955, compound

Procedure

To a mixture of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxy-carbonylmethoxyphenyl]-6-methoxy-2-methyl-7,9-dihydro-8H-purin-8-one (0.58 g) in ethanol (15 mL)-tetrahydrofuran (7.5 mL) was added sodium borohydride (0.2 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2−ethyl acetate) to give the title compound (0.52 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2−ethyl acetate)

Sources & evidence

ORD record
ord-6d0552c6da3448de9ae9a4e79478e07c
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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