p-Toluenesulfonic acid → 6-Chloro-9-isopropyl-9H-purine

HRID 1518331Notes

Reaction equation

HRID 1518331 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]([CH3:11])[CH3:10])[C:3]=1[NH2:12].[CH:13](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:12]=[CH:13][N:8]2[CH:9]([CH3:10])[CH3:11]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 71471626-Chloro-N4-isopropylpyrimidine-4,5-diamine

Product 1

HCID 4146346-Chloro-9-isopropyl-9H-purine

Conditions

Temperature
115 °C

Procedure

Compound 52A (268 mg, 1.44 mmol), triethyl orthoformate (2.4 ml, 14.36 mmol) and para-toluenesulfonic acid (27.3 mg, 0.144 mmol) were combined and heated at 115° C. overnight. Precipitation occurred upon cooling to room temperature. The precipitate was collected via filtration, rinsed with diethyl ether and dried under reduced pressure to yield the title compound 52B: 1H NMR (300 MHz, DMSO-d6) δ ppm 8.81 (1H, s), 8.78 (1H, s), 4.89 (1H, m), 1.58 (6H, d).

Workup

  1. customPrecipitation
  2. temperatureupon cooling to room temperature
  3. filtrationThe precipitate was collected via filtration
  4. washrinsed with diethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d25d24ee366342508d893b1681f020ec
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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