1-Butanol → 2-Chloro-N-(4-methoxybenzyl)-9H-purin-6-amine

HRID 1006583Notes

Reaction equation

HRID 1006583 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.CO[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].[CH2:24]([OH:28])CCC>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:28][CH3:24])=[CH:20][CH:21]=2)[N:3]=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 14798Sodium HydroxideHCID 53244122,6-DichloropurineHCID 11815413Benzyl(methoxy)amine

Product 1

HCID 164220562-Chloro-N-(4-methoxybenzyl)-9H-purin-6-amine

Conditions

Temperature
120 °C

Procedure

The 2,6-dichloropurine (4.06 g, 21.5 mmol) was suspended in n-butanol (150 ml) and the 4 methoxybenzylamine was added (3.4 ml, 26 mmol). The solution turned clear and then cloudy a few minutes later. The solution was heated at 120° C. for 2 hr and then cooled. The n-butanol was evaporated followed by suspension of the residue in water and diethyl ether mixture. A solution of 2N NaOH (1.3 ml, 26 mmol) was added and the solution stirred for 10 min before filtration. The filtered precipitate was washed with water and a small portion of ether and then dried under vacuum. The residual liquor was left overnight and more crystals were collected the next day and washed with diethyl ether.

Workup

  1. waitcloudy a few minutes
  2. temperaturecooled
  3. customThe n-butanol was evaporated
  4. additionfollowed by suspension of the residue in water
  5. washThe filtered precipitate was washed with water
  6. dry with materiala small portion of ether and then dried under vacuum
  7. waitThe residual liquor was left overnight
  8. custommore crystals were collected the next day
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ac1b782227a94241b45ebbae43423cff
Source dataset
uspto-grants-2004_09
Patent number
US06790958B2

Reaction notes

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