Hydrochloric Acid → HCID 178423287, compound

HRID 1371142Notes

Reaction equation

HRID 1371142 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1.[ClH:23].CC[O:26]C(C)=O>>[OH2:26].[ClH:23].[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423286HCID 178423286, compound

Product 1

HCID 178423287HCID 178423287, compoundYield 85%

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)-2-pyridine (freshly prepared before use) (2.20 g, 12.6 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (2.61 g, 12.6 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.2 mL, 12.6 mmol), piperidine (2.0 mL, 20.2 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (Aldrich Chemical Company) (38 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 650 mg (18%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.66 (s, 6), 2.42 (s, 3), 3.74 (s, 4), 7.01 (br s, 1), 7.37 (br s, 1), 7.90 (br s, 1), 8.08 (d, 1, J=7.9), 8.67 (br s, 1), 11.18 (s, 1). MS m/z: 294 (M+1). To a solution of 2-methyl-4-piperidyl-6-(2-pyridyl)pyrrolo[3,2-d]pyrimidine (0.65 g, 2.22 mmol) in EtOAc (30 mL) was added 1N etheral HCl (Aldrich Chemical Company) (2.20 mL, 2.22 mmol). The precipitate was collected by filtration, washed with EtOAc (2×10 mL), ether (3×15 mL) and dried under vacuum to give 621 mg (85%) of the title compound as a brown colored solid. Mp:>280° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.72 (s, 6), 2.58 (s, 3), 4.06 (br s, 4), 7.16 (s, 1), 7.51 (dd, 1, J=7.4, 7.4), 8.01 (dt, 1, J=1.4, 7.6), 8.24 (d, 1, J=7.9), 8.76 (d, 1, J=4.4), 12.19 (s, 1), 14.36 (s, 1). MS m/z: 294 (M+1). Anal. Calcd. for C17H19N5.1.2HCl.0.4H2O: C, 59.18; H, 6.14; N, 20.30; Cl, 12.53. Found C, 59.23; H, 6.14; N, 20.03; Cl, 12.56.

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-48461b095cd846a2a1492c8ea74658ed
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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