Hydrochloric Acid → HCID 178421870, compound

HRID 635697Notes

Reaction equation

HRID 635697 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][CH:15]=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH:4]([C:17]2[CH2:21][CH2:20][CH2:19][C:18]=2[CH3:22])[NH:3]1.CCOC(C)=O.[ClH:29]>CO>[ClH:29].[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][CH:15]=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH:4]([C:17]2[CH2:21][CH2:20][CH2:19][C:18]=2[CH3:22])[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178421869HCID 178421869, compound

Product 1

HCID 178421870HCID 178421870, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing [1-(2-methylcyclopent-1-enyl)vinyl]pyrrolidine (freshly prepared before use) (2.41 g, 13.6 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (2.80 g, 13.6 mmol), N,N-diisopropyl ethyl amine (Aldrich Chemical Company) (2.4 mL, 13.6 mmol), piperidine (Aldrich Chemical Company) (2.1 mL, 21.7 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 552 mg (14%) of the free base as a pale yellow colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.62 (br s, 6), 1.85-1.90 (m, 2), 1.93 (s, 3), 2.39 (s, 3), 2.79 (br s, 2), 3.30 (br s, 2), 3.67 (br s, 4), 6.23 (s, 1), 10.36 (s, 1). MS m/z: 297 (M+1). To a hot solution of 2-methyl-6-(2-methylcyclopent-1-eneyl)-4-piperidylpyrrolo[3,2-d]pyrimidine (0.55 g, 1.86 mmol) in 5:1 EtOAc:MeOH (30 mL) was added 1M etheral HCl (Aldrich Chemical Company) (1.85 mL, 1.85 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with EtOAc (1×5 mL), Et2O (3×10 mL) and dried under vacuum to give 580 mg (94%) of the title compound as a white colored solid. Mp: 224.5-226° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.69 (br s, 6), 1.89-1.93 (m, 5), 2.50 (s, 3), 2.82 (br s, 2), 3.31 (s, 2), 3.99 (br s, 4), 6.39 (s, 1), 11.49 (s, 1), 14.34 (s, 1). MS m/z: 297 (M+1). Anal. Calcd for C18H24N4.HCl: C, 64.95; H, 7.57; N, 16.83; Cl, 10.65. Found C, 64.72; H, 7.63; N, 16.65; Cl, 10.37.

Workup

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

Sources & evidence

ORD record
ord-f240d879c8854da6a67ade09d9b26823
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

Loading…