Hydrochloric Acid → HCID 178430024, compound

HRID 1371152Notes

Reaction equation

HRID 1371152 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6]=1[NH:7][C:8]([CH:11]1[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:14][CH2:13][CH2:12]1)=[N:9][CH:10]=2.CCOC(C)=O.[ClH:29]>CO>[ClH:29].[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6]=1[NH:7][C:8]([CH:11]1[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:14][CH2:13][CH2:12]1)=[N:9][CH:10]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178430023HCID 178430023, compound

Product 1

HCID 178430024HCID 178430024, compoundYield 93.3%

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) (2.10 g, 11.3 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.18 g, 11.3 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.0 mL, 11.3 mmol), piperidine (1.8 mL, 18.1 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (Aldrich Chemical Company) (34 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 407 mg (12%) of the product as a faint yellow colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.64 (br s, 6), 2.30 (s, 3), 3.72 (br S, 4), 7.44 (t, 1, J=7.3), 7.53 (t, 2, J=7.53), 7.66 (d, 2, J=7.3), 8.29 (s, 1), 10.95 (s, 1). MS m/z: 293 (M+1). To a solution of 7-methyl-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: 281-282.5° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 2.32 (s, 3), 4.04 (br s, 4), 7.52-7.61 (m, 3), 7.68 (d, 2, J=7.1), 8.56 (s, 1), 12.05 (s, 1), 14.67 (s, 1). MS m/z: 293 (M+1). Anal. Calcd. for C24H24N4.HCl: C, 65.74; H, 6.44; N, 17.04; Cl, 10.78. Found C, 65.64; H, 6.51; N, 17.04; Cl, 10.71.

Workup

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

Sources & evidence

ORD record
ord-ea2a44c2f6064d1797a5b90cec1255ab
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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