1-Bromo-3-chloropropane → HCID 67456356, compound

HRID 1713320Notes

Reaction equation

HRID 1713320 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[NH:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:45]([OH:55])[CH:44]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:63][CH2:64][CH2:65][Cl:66]>CN(C)C=O>[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])[C@@H:12]([CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:25])[CH3:26])[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[NH:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[C:45]([O:55][CH2:63][CH2:64][CH2:65][Cl:66])[CH:44]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 67454990HCID 67454990, compound

Product 1

HCID 67456356HCID 67456356, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2′,3′,5′-tris-O-(tert-butyl-dimethylsilyl)-8-(2-hydroxybiphenyl-4-ylmethylamino)-adenosine (0.85 g) in N,N-dimethylformamide (5.3 mL) was added potassium carbonate (0.44 g). Then 1-bromo-3-chloropropane (0.16 mL) was added, and the resulting mixture was stirred at 40° C. for 42 hours. The reaction mixture was partitioned between diethyl ether (45 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2), and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.91 g).

Workup

  1. customThe reaction mixture was partitioned between diethyl ether (45 mL) and water (10 mL)
  2. washThe organic layer was washed successively with water (10 mL×2), and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0d7261f83c64b3fadaa497744c36df0
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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