Hydrochloric Acid → HCID 178479637, compound

HRID 1371147Notes

Reaction equation

HRID 1371147 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:12][C:11]3=[CH:13][C:14]([C:16]4[CH:21]=[N:20][CH:19]=[CH:18][N:17]=4)=[N:15][C:10]3=[CH:9][N:8]=2)[CH2:3][CH2:2]1.CC[O:24]C(C)=O.[ClH:28]>CO>[OH2:24].[ClH:28].[NH:1]1[CH2:2][CH2:3][CH:4]([C:7]2[NH:12][C:11]3=[CH:13][C:14]([C:16]4[CH:21]=[N:20][CH:19]=[CH:18][N:17]=4)=[N:15][C:10]3=[CH:9][N:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178420755HCID 178420755, compound

Product 1

HCID 178479637HCID 178479637, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)pyrazine (freshly prepared before use) (2.39 g, 13.7 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.60 g, 13.7 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.4 mL, 13.7 mmol), piperidine (Aldrich Chemical Company) (2.2 mL, 21.9 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (41 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 143 mg (4%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.67 (br s, 6), 3.77 (s, 4), 7.28 (s, 1), 8.28 (s, 1), 8.63 (s, 1), 8.74 (s, 1), 9.36 (s, 1), 11.48 (s, 1). MS m/z: 281 (M+1). To a hot solution of 4-piperidyl-6-pyrazin-2-ylpyrrolo[3,2-d]pyrimidine (0.14 g, 0.51 mmol) in 10:1 EtOAc:MeOH (40 mL) was added 1M etheral HCl (Aldrich Chemical Company) (0.51 mL, 0.51 mmol). Cyrstallization occurred as the mixture cooled and the precipitate was collected by filtration. The crystals were washed with Et2O (3×10 mL) and dried under vacuum to give 128 mg (80%) of the title compound as a beige colored solid. Mp:>280° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.73 (s, 6), 4.10 (s, 4), 7.37 (s, 1), 8.66 (s, 1), 8.75 (d, 1, J=2.5), 8.83 (t, 1, J=1.5), 9.49 (d, 1, J=1.2), 12.53 (s, 1), 14.56 (s, 1). MS m/z: 281 (M+1). Anal. Calcd for C15H16N6.HCl.0.25H2O: C, 56.00; H, 5.49; N, 26.13; Cl, 11.10. Found C, 56.00; H, 5.49; N, 26.11; Cl, 11.09.

Workup

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

Sources & evidence

ORD record
ord-f3e5e5a853eb4473ab64cd2284555634
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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