Thionyl Chloride → 6-Amino-9-(2-chloroethyl)-8-(2-pyridin-3-yl-ethyl)-purine

HRID 1920656Notes

Reaction equation

HRID 1920656 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[N:6]2[CH2:11][CH2:12]O.O=S(Cl)[Cl:24]>>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[N:6]2[CH2:11][CH2:12][Cl:24]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 668676282-(6-Amino-8-(2-pyridin-3-yl-ethyl)-purin-9-yl)ethanol

Product 1

HCID 668679646-Amino-9-(2-chloroethyl)-8-(2-pyridin-3-yl-ethyl)-purineYield 8%

Procedure

0.45 g of 2-(6-amino-8-(2-pyridin-3-yl-ethyl)-purin-9-yl)ethanol were cooled to −20° C. and 6 ml of SOCl2 were added. The temperature was gradually risen to 50° C. and the mixture was stirred at this temperature for 12 hours. The excess of SOCl2 was evaporated and the residue was taken up in dichloromethane washed with saturated aqueous NaHCO3 dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (CHCl3:MeOH 50:1) to give 40 mg (8%) of the desired product.

Workup

  1. customwas gradually risen to 50° C.
  2. customThe excess of SOCl2 was evaporated
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel (CHCl3:MeOH 50:1)

Sources & evidence

ORD record
ord-df08aa149db34b8a89707d2ddcc7b2c1
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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