Hydrochloric Acid → HCID 178479624, compound

HRID 635686Notes

Reaction equation

HRID 635686 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:12][C:11]3=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)=[N:15][C:10]3=[CH:9][N:8]=2)[CH2:3][CH2:2]1.CC[O:24]C(C)=O.[ClH:28]>CO>[OH2:24].[ClH:28].[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:12][C:11]3=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)=[N:15][C:10]3=[CH:9][N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178420056HCID 178420056, compound

Product 1

HCID 178479624HCID 178479624, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)-2-pyridine (freshly prepared before use) (2.30 g, 13.2 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.55 g, 13.2 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.3 mL, 13.2 mmol), piperidine (2.1 mL, 21.1 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (Aldrich Chemical Company) (40 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 340 mg (9%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.66 (s, 6), 3.76 (s, 4), 7.13 (br s, 1), 7.41 (t, 1, J=4.8), 7.92 (t, 1, J=7.4), 8.10 (d, 1, J=8.0), 8.26 (br s, 1), 8.70 (br s, 1), 11.24 (s, 1). MS m/z: 280 (M+1). To a solution of 4-piperidyl-6-(2-pyridyl)pyrrolo[3,2-d]pyrimidine (0.34 g, 1.21 mmol) in 15:1 EtOAc:MeOH (30 mL) was added 1N etheral HCl (Aldrich Chemical Company) (1.20 mL, 1.21 mmol). The precipitate was collected by filtration, washed with EtOAc (2×10 mL), ether (3×15 mL) and dried under vacuum to give 300 mg (79%) of the title compound as a tan colored powder. Mp: 279-280° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.72 (s, 6), 4.0 (br s, 4), 7.24 (s, 1), 7.52 (dd, 1, J=7.4, 7.5), 8.01 (dt, 1, J=1.3, 7.7), 8.24 (d, 1, J=8.0), 8.64 (s, 1), 8.77 (d, 1, J=4.4), 12.21 (s, 1), 14.51 (s, 1). MS m/z: 280 (M+1). Anal. Calcd for C16H17N5.1.2HCl.0.7H2O: C, 56.91; H, 5.88; N, 20.75; Cl, 13.01. Found C, 56.91; H, 5.83; N, 20.54; Cl, 12.92.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with EtOAc (2×10 mL), ether (3×15 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-59a4af7a27b84002886c9c53bc4f7191
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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