Bromoform → HCID 66623575, compound

HRID 1831463Notes

Reaction equation

HRID 1831463 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:6][C:5]=2[N:26]=1.C(ON=O)CC(C)C.C(Br)(Br)[Br:36]>C(#N)C>[C:20]1([CH2:19][S:18][C:7]2[N:8]=[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])[C:4]3[S:3][C:2]([Br:36])=[N:26][C:5]=3[N:6]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 5558BromoformHCID 8053Isoamyl NitriteHCID 58230405HCID 58230405, compound

Product 1

HCID 66623575HCID 66623575, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of (R)-2-(2-amino-5-phenylmethylthio-thiazolo[4,5-d]pyrimidin-7-ylamino)-4-methyl-pentan-1-ol (WO 00/09511) (131 mg, 0.34 mmol) in bromoform (6 mL) and anhydrous acetonitrile (2.5 mL), isoamylnitrite (158 μL, 1.2 mmol) was added. The mixture was heated at 60° C. under a nitrogen atmosphere for 30 minutes followed by evaporation of the solvent. The crude, red solid was flash chromatographed on silica (eluent—ethyl acetate:dichloromethane, 10:90) and the product was dried in vacuo at 50° C. overnight, resulting in 61 mg (40% yield) of the title compound as a brown solid.

Workup

  1. additionwas added
  2. customfollowed by evaporation of the solvent
  3. customchromatographed on silica (eluent—ethyl acetate:dichloromethane, 10:90)
  4. customthe product was dried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-af8dac3779d3498fb1874e6cadd76c15
Source dataset
uspto-grants-2006_06
Patent number
US07067657B2

Reaction notes

Loading…