Hydrochloric Acid → HCID 178423307, compound

HRID 635699Notes

Reaction equation

HRID 635699 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[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[NH:3]1.CC[O:31]C(C)=O.[ClH:35]>CO>[OH2:31].[ClH:35].[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[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423306HCID 178423306, compound

Product 1

HCID 178423307HCID 178423307, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing [1-(4-phenylphenyl)vinyl]pyrrolidine (freshly prepared before use) (1.35 g, 5.42 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.21 g, 5.42 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (0.9 mL, 5.42 mmol), piperidine (Aldrich Chemical Company) (0.9 mL, 8.67 mmol), NEt3 (Aldrich Chemical Company) (1.0 mL) and SnCl2 (Aldrich Chemical Company) (16 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 220 mg (11%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.67 (br s, 6), 2.43 (s, 3), 3.74 (br s, 4), 6.80 (s, 1), 7.39 (t, 1, J=7.2), 7.50 (t, 2, J=7.7), 7.75 (d, 2, J=7.5), 7.78 (d, 2, J=7.6), 8.00 (d, 2, J=8.2), 11.01 (s, 1). MS m/z: 369 (M+1). To a hot solution of 2-methyl-6-(4-phenylphenyl)-4-piperidyl pyrrolo[3,2-d]pyrimidine (0.22 g, 0.59 mmol) in 10:1 EtOAc: MeOH (40 mL) was added 1N etheral HCl (Aldrich Chemical Company) (600 mL, 0.60 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (3×5 mL) and dried under vacuum to give 205 mg (86%) of the title compound as a pale yellow colored solid. Mp: >280° C. 1H NMR (DMSO-d6; 500 MHz): δ 1.72 (br s, 6), 2.58 (s, 3), 4.07 (br s, 4), 6.96 (s, 1), 7.43 (t, 1, J=7.2), 7.42 (t, 2, J=7.7), 7.77 (d, 2, J=7.9), 7.86 (d, 2, J=8.1), 8.06 (d, 2, J=8.1), 12.00 (s, 1), 14.29 (s, 1). MS m/z: 369 (M+1). Anal. Calcd for C24H24N4.HCl.1.0H2O: C, 67.92; H, 6.45; N, 13.21; Cl, 8.35. Found C, 67.92; H, 6.43; N, 13.17; Cl, 8.46.

Workup

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

Sources & evidence

ORD record
ord-a8b760dc38ca4048bf0b24c969075a0e
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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