Hydrogen Bromide → HCID 87285362, compound

HRID 1270274Notes

Reaction equation

HRID 1270274 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][O:10][C@@H:11]1[C@@H:17]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[O:16][C@H:13](OC)[C@:12]1([CH:30]=[CH2:31])[OH:29].Br.[Na].[Cl:34][C:35]1[N:40]=[CH:39][NH:38][C:37]2=[N:41][CH:42]=[CH:43][C:36]=12>ClCCl.NC1C2C=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@@]3(C)O)C=2N=CN=1>[Cl:34][C:35]1[C:36]2[CH:43]=[CH:42][N:41]([C@@H:13]3[O:16][C@H:17]([CH2:11][O:10][CH2:9][C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])[C@@H:18]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C@@:12]3([CH:30]=[CH2:31])[OH:29])[C:37]=2[N:38]=[CH:39][N:40]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 5360545SodiumHCID 671428963,5-Bis-o-(2,4-dichlorobenzyl)-2-c-vinyl-1-o-methyl-alpha-d-ribofuranoseHCID 178418725HCID 178418725, compound

Product 1

HCID 87285362HCID 87285362, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 30118937-Deaza-2'-C-methyladenosineSolvent

Procedure

To a solution of the compound from Step A (6.4 g, 12.6 mmol) in anhydrous dichloromethane (150 mL) at −20° C. was added HBr (30% solution in AcOH, 20 mL, 75.6 mmol) dropwise. The resulting solution was stirred between −10° C. and 0° C. for 4 h, evaporated in vacuo and co-evaporated with anhydrous toluene (3×40 mL). The oily residue was dissolved in anhydrous acetonitrile (100 mL) and added to a solution of the sodium salt of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (5.8 g, 37.8 mmol) in acetonitrile (generated in situ as described in Example 62) at −20° C. The resulting mixture was allowed to come to room temperature and stirred at room temperature for 24 h. The mixture was then evaporated to dryness, taken up in water and extracted with EtOAc (2×300 mL). The combined extracts were dried over Na2SO4, filtered and evaporated. The crude mixture was purified by flash chromatography (SiO2, 10% EtOAc in hexanes) and the title compound (1.75 g) isolated as a white foam.

Workup

  1. customevaporated in vacuo and co-evaporated with anhydrous toluene (3×40 mL)
  2. dissolutionThe oily residue was dissolved in anhydrous acetonitrile (100 mL)
  3. customto come to room temperature
  4. stirringstirred at room temperature for 24 h
  5. customThe mixture was then evaporated to dryness
  6. extractionextracted with EtOAc (2×300 mL)
  7. dry with materialThe combined extracts were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude mixture was purified by flash chromatography (SiO2, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7c3f905898e544f3b14ac6cf685d3474
Source dataset
uspto-grants-2007_04
Patent number
US07202224B2

Reaction notes

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