Trifluoroacetic acid → 2-Chloro-8-(2,2-dimethylpiperazin-1-ylmethyl)-9-methyl-6-morpholin-4-yl-9H-purine

HRID 1922835Notes

Reaction equation

HRID 1922835 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[N:16]([CH3:31])[C:17]3[C:22]([N:23]=2)=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:20]=[C:19]([Cl:30])[N:18]=3)[C:10]([CH3:33])([CH3:32])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:30][C:19]1[N:18]=[C:17]2[C:22]([N:23]=[C:15]([CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]3([CH3:33])[CH3:32])[N:16]2[CH3:31])=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596057974-(2-Chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596054502-Chloro-8-(2,2-dimethylpiperazin-1-ylmethyl)-9-methyl-6-morpholin-4-yl-9H-purine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (288 mg, 0.60 mmol) in DCM (30 mL) was added TFA (3 mL) and the mixture stirred at r.t for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording the title compound as a white solid (199 mg, 87%). 1H NMR (CDCl3, 400 MHz): δ 4.26 (4 H, brd s), 3.84-3.77 (9 H, m), 2.84 (2 H, t, J=4.87 Hz), 2.74 (2 H, s), 2.43 (2 H, t, J=4.89 Hz), 1.21 (6 H, s).

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH affording the title compound as a white solid (199 mg, 87%)

Sources & evidence

ORD record
ord-1798116173b84cbc82114ce083e4292f
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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