Hydrochloric Acid → HCID 178422582, compound

HRID 1371156Notes

Reaction equation

HRID 1371156 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:23])=[CH:5][C:6]=1[C:7]1[CH:22]=[C:10]2[NH:11][C:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]3)=[N:13][CH:14]=[C:9]2[N:8]=1.CC[O:26]C(C)=O.[ClH:30]>CO>[OH2:26].[ClH:30].[CH3:1][C:2]1[S:3][C:4]([CH3:23])=[CH:5][C:6]=1[C:7]1[CH:22]=[C:10]2[NH:11][C:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]3)=[N:13][CH:14]=[C:9]2[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178422581HCID 178422581, compound

Product 1

HCID 178422582HCID 178422582, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2,5-dimethyl-3-(1-pyrrolidinylvinyl)thiophene (freshly prepared before use) (1.40 g, 6.76 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.40 g, 6.76 mmol), N,N-diisopropyl ethyl amine (Aldrich Chemical Company) (1.2 mL, 6.76 mmol), piperidine (Aldrich Chemical Company) (1.1 mL, 10.8 mmol), NEt3 (Aldrich Chemical Company) (1.0 mL) and SnCl2 (20 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 335 mg (15%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.63 (br s, 6), 2.40 (s, 3), 2.42 (s, 3), 2.50 (s, 3), 3.70 (br s, 4), 6.36 (s, 1), 7.04 (s, 1), 10.82 (s, 1). MS m/z: 327 (M+1). To a hot solution of 2,5-dimethyl-3-(2-methyl-4-piperidyl pyrrolo[4,5-d]pyrimidin-6-yl)thiophene (0.35 g, 1.02 mmol) in 5:1 EtOAc:MeOH (40 mL) was added 1M etheral HCl (Aldrich Chemical Company) (1.00 mL, 1.00 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (2×5 mL) and dried under vacuum to give 222 mg (60%) of the title compound as a beige colored solid. Mp: 240-241.5° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.70 (br s, 6), 2.44 (s, 3), 2.50 (s, 3), 2.55 (s, 3), 4.02 (br s, 4), 6.54 (s, 1), 7.06 (s, 1), 11.89 (s, 1), 14.15 (s, 1). MS m/z: 327 (M+1). Anal. Calcd for C18H22N4S.HCl.1.5H2O: C, 55.53; H, 6.68; N, 14.40; Cl, 9.00; S, 8.23. Found C, 55.62; H, 6.66; N, 14.31; Cl, 9.31; S, 8.28.

Workup

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

Sources & evidence

ORD record
ord-023bc03c65b3411fa9c900a2f13a603a
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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