Hydrochloric Acid → HCID 178423299, compound

HRID 635688Notes

Reaction equation

HRID 635688 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[CH:22]=[N:21][CH:20]=[CH:19][N:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1.CC[O:25]C(C)=O.[ClH:29]>CO>[OH2:25].[ClH:29].[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[CH:22]=[N:21][CH:20]=[CH:19][N:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423298HCID 178423298, compound

Product 1

HCID 178423299HCID 178423299, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)pyrazine (freshly prepared before use) (2.15 g, 12.3 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (2.50 g, 12.3 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.1 mL, 12.3 mmol), piperidine (Aldrich Chemical Company) (1.9 mL, 19.7 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (37 mL of a 2M solution in DMF). The residue was purified by flash chromatography on silica gel with 95:5 CHCl3:MeOH as elutant to give 116 mg (4%) of the free base as a brown colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.66 (br s, 6), 2.44 (s, 3), 3.30 (s, 2, under H2O), 3.77 (br s, 2), 6.80-7.15 (m, 1), 8.91 (br s, 2), 9.33 (s, 1), 11.42 (s, 1). MS m/z: 295 (M+1). To a hot solution of 2-methyl-4-piperidyl-6-pyrazin-2-ylpyrrolo[3,2-d]pyrimidine (0.12 g, 0.39 mmol) in 10:1 EtOAc:MeOH (30 mL) was added 1N etheral HCl (Aldrich Chemical Company) (0.40 mL, 0.39 mmol). Cyrstallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (3×10 mL), and dried under vacuum to give 68 mg (53%) of the title compound as a brown colored solid. Mp: 280-283.5° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.72 (s, 6), 2.59 (s, 3), 4.08 (br s, 4), 7.29 (s, 1), 8.74 (d, 1, J=2.4), 8.82 (br s, 1), 9.49 (s, 1), 12.41 (s, 1), 14.41 (s, 1). MS m/z: 295 (M+1 for free base). Anal. Calcd for C16H16N6.HCl.1.4H2O: C, 54.07; H, 5.64; N, 23.65; Cl, 10.19. Found C, 54.32; H, 5.69; N, 23.26; Cl, 10.18.

Workup

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

Sources & evidence

ORD record
ord-c499c24943ad4ec987a9dc4e8a361dff
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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