Sodium borohydride → HCID 67150706, compound

HRID 549781Notes

Reaction equation

HRID 549781 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH:4]=[CH:5][CH:6]1[CH:13]2[CH:9]([O:10][CH:11]([CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12]2)[CH:8]([N:22]2[CH:30]=[N:29][C:28]3[C:23]2=[N:24][CH:25]=[N:26][C:27]=3[NH:31][C:32]([NH:34][CH2:35][CH3:36])=[O:33])[O:7]1.[BH4-].[Na+]>CO.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][CH:6]1[CH:13]2[CH:9]([O:10][CH:11]([CH:14]=[CH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:12]2)[CH:8]([N:22]2[CH:30]=[N:29][C:28]3[C:23]2=[N:24][CH:25]=[N:26][C:27]=3[NH:31][C:32]([NH:34][CH2:35][CH3:36])=[O:33])[O:7]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67150729HCID 67150729, compound

Product 1

HCID 67150706HCID 67150706, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-{6-[6-(3-Ethyl-ureido)-purin-9-yl]-2-styryl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-acrylic acid methyl ester (250 mg, 0.5 mmol) was dissolved in dry methanol (3 mL). Copper (II) sulfate (90 mg, 0.5 mmol) was added followed by sodium tetrahydroborate (90 mg, 2.5 mmol) and the reaction was stirred 48 h. The reaction was diluted with water, filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate and precipitated with heptane. The precipitate was dissolved in dichloromethane and was chromatographed on silica gel with dichloromethane-methanol (95:5) as eluent, affording the title compound (125 mg, 50%). 1H-NMR (300 MHz, d6 DMSO) 1.15 (t, 3H, J=7 Hz), 1.90 (m, 2H), 2.19 (m, 2H), 3.21 (q, 2H, J=7 Hz), 3.55 (s, 3H), 4.20 (m, 1H), 4.98 (dd, 1H, J=4 Hz, 6 Hz), 5.45 (dd, 1H, J=3 Hz, 7 Hz), 5.85 (d, 1H, J=6 Hz), 6.25 (d, 1H, J=3 Hz), 6.27 (dd, 1H, J=6 Hz, 16 Hz), 6.90 (d, 1H, J=16 Hz), 7.35 (m, 3H), 7.50 (d, 2H, J=7 Hz), 8.56 (s, 1H), 8.57 (s, 1H), 9.30 (t, 1H, J=5 Hz), 9.60 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customprecipitated with heptane
  5. dissolutionThe precipitate was dissolved in dichloromethane
  6. customwas chromatographed on silica gel with dichloromethane-methanol (95:5) as eluent

Sources & evidence

ORD record
ord-b05b4320366b4603b2e67aab530c6d8d
Source dataset
uspto-grants-2011_05
Patent number
US07943760B2

Reaction notes

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