Hydrochloric Acid → HCID 178430016, compound

HRID 1371153Notes

Reaction equation

HRID 1371153 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[C:14]([CH3:17])[CH:15]=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:3]1.CC[O:26]C(C)=O.[ClH:30]>CO>[OH2:26].[ClH:30].[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[C:14]([CH3:17])[CH:15]=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178430015HCID 178430015, compound

Product 1

HCID 178430016HCID 178430016, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing (1-phenylbut-1-enyl)pyrrolidine (freshly prepared before use) (2.13 g, 11.5 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.30 g, 11.5 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.0 mL, 11.5 mmol), piperidine (1.8 mL, 18.4 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (Aldrich Chemical Company) (35 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 304 mg (9%) of the free base as a beige colored fluffy solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.63 (br s, 6), 2.27 (s, 3), 2.44 (s, 3), 3.71 (br s, 4), 7.43 (t, 1, J=7.3), 7.52 (t, 2, J=7.6), 7.65 (d, 2, J=7.4), 10.79 (s, 1). MS m/z: 307 (M+1). To a solution of 2,7-dimethyl-6-phenyl-4-piperidylpyrrolo[3,2-d]pyrimidine (0.22 g, 0.76 mmol) in 5:1 EtOAc:MeOH (30 mL) was added 1M etheral HCl (Aldrich Chemical Company) (760 mL, 0.73 mmol). The precipitate was collected by filtration, washed with ether (3×15 mL) and dried under vacuum to give 224 mg (90%) of the title compound as a white colored solid. Mp:>280° C. 1H NMR (DMSO-d6; 400 MHz) δ 1.69 (br s, 6), 2.35 (s, 3), 2.64 (s, 3), 4.03 (br s, 4), 7.52-7.60 (m, 3), 7.65-7.68 (m, 2), 11.94 (s, 1), 14.16 (s, 1). MS m/z: 307 (M+1). Anal. Calcd. for C24H24N4.1.1HCl.H2O: C, 62.74; H, 6.95; N, 15.41; Cl, 10.50. Found C, 63.09; H, 7.00; N, 15.39; Cl, 10.54.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ether (3×15 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4e845bb88338403ca2180c4be4a8c1de
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

Loading…