2-Butyne-1,4-diol → HCID 21278113, compound

HRID 2291857Notes

Reaction equation

HRID 2291857 reaction equation
Br[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].C(O)C#CCO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:34][C:35]1[N:43]=[C:42]2[C:38]([NH:39][CH:40]=N2)=[C:37]([Cl:44])[N:36]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C)C=O>[NH2:34][C:35]1[N:43]=[C:42]2[C:38]([N:39]=[CH:40][N:2]2[CH2:6][C:5]#[C:4][CH2:3][OH:8])=[C:37]([Cl:44])[N:36]=1

Participants

8

Reactant 5

HCID 80662-Butyne-1,4-diolHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 53603492-Amino-6-chloropurine

Product 1

HCID 21278113HCID 21278113, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (1.78 g, 10 mmol) was added in portions to a stirred suspension of 2-butyne-1,4-diol (2.50 g, 30 mmol) and triphenylphosphine (2.62 g, 10 mmol) in 20 ml of dichloromethane at room temperature. After 1 h, the unreacted butynediol was removed by filtration. The solution was evaporated in vacuum to small volume, dissolved in 20 ml of dry dimethylformamide (DMF) and added to a suspension of 2-amino-6-chloropurine (1.70 g, 10 mmol) and finely ground anhydrous K2CO3 (2.07 g, 15 mmol) in 75 ml of dry DMF, stirred at 0° C. The stirring was continued at room temperature for 3 days. Then the mixture was evaporated in vacuum to dryness. Chromatography (silica gel, CHCl3 +MeOH 7+1) afforded 467 mg (20%; after recrystallization from water to remove 2-butyne-1,4-diol) of 4-(2-amino-6-chloropurin-9-yl)-2-butyn-1-ol (TLC on silica gel, CHCl3 +MeOH 5+1; Rf 0.57).

Workup

  1. customthe unreacted butynediol was removed by filtration
  2. customThe solution was evaporated in vacuum to small volume
  3. dissolutiondissolved in 20 ml of dry dimethylformamide (DMF)
  4. waitThe stirring was continued at room temperature for 3 days
  5. customThen the mixture was evaporated in vacuum to dryness

Sources & evidence

ORD record
ord-7030efcfb22345eab989b3db54dc40b6
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

Loading…