Boron Trichloride → (2R,3R,4R,5R)-2-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol

HRID 2212950Notes

Reaction equation

HRID 2212950 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28]CC4C=CC(Cl)=CC=4Cl)[C@@H:14]([O:15]CC4C=CC(Cl)=CC=4Cl)[C@@:12]3([CH3:38])[OH:13])[N:9]=[CH:10][C:3]=12.B(Cl)(Cl)Cl>ClCCl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:14]([OH:15])[C@@:12]3([CH3:38])[OH:13])[N:9]=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 112963434-Amino-1-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-methyl-beta-d-ribofuranosyl]-1h-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 3011894(2R,3R,4R,5R)-2-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diolYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the compound from Step A (0.20 g, 0.33 mmol) in dichloromethane (10 mL) at −78° C. was added boron trichloride (1M in dichloromethane) (3 mL, 3 mmol) dropwise. The mixture was stirred at −78° C. for 0.5 h, then at −45° C. to −30° C. for 2 h. The reaction was quenched by addition of sodium acetate (1.0 g) and methanol (10 mL). The solution was evaporated and the residue was purified by flash chromatography over silica gel using CH2Cl2 and CH2Cl2/MeOH (95:5-90:10) gradient as the eluent to furnish the desired compound (60 mg) as a solid, which was recrystallized from methanol and acetonitrile to give the title compound as an off-white solid (40 mg).

Workup

  1. waitat −45° C. to −30° C. for 2 h
  2. customThe reaction was quenched by addition of sodium acetate (1.0 g) and methanol (10 mL)
  3. customThe solution was evaporated
  4. customthe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-b96420399bc948ecb9673ff5e3760537
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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