Hydrochloric Acid → HCID 178423322, compound

HRID 1371154Notes

Reaction equation

HRID 1371154 reaction equation
[C:1]([CH:5]1[NH:10][CH:9]([CH3:11])[CH2:8][CH:7]([C:12]2[NH:17][C:16]3=[CH:18][CH:19]=[N:20][C:15]3=[CH:14][N:13]=2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].CC[O:23]C(C)=O.[ClH:27]>CO>[OH2:23].[ClH:27].[C:1]([CH:5]1[NH:10][CH:9]([CH3:11])[CH2:8][CH:7]([C:12]2[NH:17][C:16]3=[CH:18][CH:19]=[N:20][C:15]3=[CH:14][N:13]=2)[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423321HCID 178423321, compound

Product 1

HCID 178423322HCID 178423322, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 1-(tert-butyl)vinylpyrrolidine (freshly prepared before use) (1.20 g, 7.73 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.60 g, 7.73 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.3 mL, 7.73 mmol), piperidine (Aldrich Chemical Company) (1.2 mL, 12.4 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (23 mL of a 2M solution in DMF). The crude residue was purified by flash chromatography on silica gel with 95:5 CHCl3:MeOH as elutant to give 448 mg (21%) of the free base as a cream colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.36 (s, 9), 1.63 (br s, 6), 2.38 (s, 3), 3.60 (br s, 4), 6.05 (d, 1, J=1.6), 10.20 (s, 1). MS m/z: 273 (M+1). To a hot solution of 6-(tert-butyl)-2-methyl-4-piperidylpyrrolo[3,2-d]pyrimidine (0.45 g, 1.65 mmol) in 10:1 EtOAc:MeOH (30 mL) was added 1N etheral HCl (Aldrich Chemical Company) (1.70 mL, 1.65 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (3×10 mL) and dried under vacuum to give 420 mg (83%) of the title compound as a white colored solid. Mp: 256-258° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.41 (s, 9), 1.67 (m, 6), 2.54 (s, 3), 3.98 (t, 4, J=5.2), 6.26 (s, 1), 11.14 (s, 1), 14.32 (s, 2). MS m/z: 273 (M+1). Anal. Calcd for C16H25ClN4.0.25H2O: C, 61.41; H, 8.20; N, 17.91; Cl, 11.33. Found C, 61.41; H, 8.11; N, 17.90; Cl, 11.39.

Workup

  1. customCrystallization
  2. temperaturecooled
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with Et2O (3×10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b5deda556b55440f9bc8f72df14c8810
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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