Thionyl Chloride → 6-Amino-9-(2-chloroethyl)-8-[(3-pyridinylmethyl)amino]-9H-purine

HRID 2112399Notes

Reaction equation

HRID 2112399 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH: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.S(Cl)([Cl:24])=O>>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH: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 688816656-Amino-9-(2-hydroxyethyl)-8-[(3-pyridinylmethyl)amino]-9H-purine

Product 1

HCID 688809636-Amino-9-(2-chloroethyl)-8-[(3-pyridinylmethyl)amino]-9H-purineYield 53%

Conditions

Temperature
50 °C

Procedure

A mixture of 350 mg (1.22 mmol) 6-amino-9-(2-hydroxyethyl)-8-[(3-pyridinyl-methyl)amino]-9H-purine and 2 ml of thionylchloride was stirred at 50° C. After completion of the reaction (˜3h) the mixture was concentrated in vacuo and subsequently diluted with water and the pH was adjusted to pH 7 with ammonia. The precipitate was isolated, washed with water, ethyl acetate and diethylether to give 197 mg (53%) of the desired product. 1H-NMR (DMSO): 8.62 (s, 1H), 8.44 (d, 1H), 7.92 (s, 1H), 7.80 (d, 1H), 7.38 (t, 1H), 7.33 (m, 1H, NH), 6.32 (s, 2H, NH2), 4.60 (d, 2H), 4.34 (t, 2H), 3.92 (t, 2H).

Workup

  1. customAfter completion of the reaction (˜3h) the mixture
  2. concentrationwas concentrated in vacuo
  3. additionsubsequently diluted with water
  4. customThe precipitate was isolated
  5. washwashed with water, ethyl acetate and diethylether

Sources & evidence

ORD record
ord-660d71e1293843a2947566fba4d06ddf
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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