Boron Trichloride → 5-amino-3-(beta-D-arabinofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione

HRID 2248944Notes

Reaction equation

HRID 2248944 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:42])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:32][C@H:31]([CH2:33][O:34]CC4C=CC=CC=4)[C@@H:22]([O:23]CC4C=CC=CC=4)[C@@H:13]3[O:14]CC3C=CC=CC=3)[C:6]=2[N:7]=1.B(Cl)(Cl)Cl>ClCCl>[NH2:1][C:2]1[NH:3][C:4](=[O:42])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:32][C@H:31]([CH2:33][OH:34])[C@@H:22]([OH:23])[C@@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 1361975895-Amino-3-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione

Product 1

HCID 1361261045-amino-3-(beta-D-arabinofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

Compound 39 is dissolved in dry dichloromethane and deprotected using an excess of boron trichloride (1M in dichloromethane) at -78° C. and allowed to warm to -40° C. for 2 hours before quenching with methanol. The residue after workup is crystallized from water to yield 40 as a colorless crystalline solid.

Workup

  1. customat -78° C.
  2. custombefore quenching with methanol
  3. customThe residue after workup is crystallized from water

Sources & evidence

ORD record
ord-894e3069799a406f8476c8dfdde12415
Source dataset
uspto-grants-1991_08
Patent number
US05041426

Reaction notes

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