Hydrochloric Acid → HCID 178478296, compound

HRID 1371143Notes

Reaction equation

HRID 1371143 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[S:17][CH:18]=[CH:19][CH:20]=4)=[N:15][C:10]3=[CH:9][N:8]=2)[CH2:3][CH2:2]1.CCOC(C)=O.[ClH:27]>CO>[ClH:27].[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:12][C:11]3=[CH:13][C:14]([C:16]4[S:17][CH:18]=[CH:19][CH:20]=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 178420842HCID 178420842, compound

Product 1

HCID 178478296HCID 178478296, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)thiophene (freshly prepared before use) (1.80 g, 10.1 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (1.95 g, 10.1 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.8 mL, 10.1 mmol), piperidine (2.0 mL, 20.3 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (30 mL of a 2M solution in DMF). The residue was purified by flash chromatography on silica gel with 97:3 CHCl3:MeOH as elutant to give 460 mg (16%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.72 (s, 6), 3.83 (s, 4), 6.69 (br s, 1), 7.25 (t, 1, J=3.9), 7.69 (br s, 1), 7.75 (br s, 1), 8.30 (s, 1), 11.34 (s, 1). MS m/z: 285 (M+1) To a solution of 2-(4-Piperidylpyrrolo[4,5-d]pyrimidin-6-yl)thiophene (0.46 g, 1.63 mmol) in 10:1 EtOAc:MeOH (30 mL) was added 1N etheral HCl (Aldrich Chemical Company) (1.63 mL, 1.63 mmol). The precipitate was collected by filtration, washed with EtOAc (2×10 mL), ether (3×15 mL) and dried under vacuum to give 462 mg (88%) of the title compound as a beige colored solid. Mp:>280° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (s, 6), 4.05 (br s, 4), 6.77 (s, 1), 7.26 (t, 1, J=4.6), 7.80 (d, 1, J=5.0), 7.89 (d, 1, J=3.6), 8.59 (s, 1), 12.45 (s, 1), 14.42 (s, 1). MS m/z: 285 (M+1 for free base). Anal. Calcd for C15H16N4S.HCl: C, 56.15; H, 5.34; N, 17.46; Cl, 11.05. Found C, 55.86; H 5.32; N, 17.27; Cl, 11.29.

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-c4304cffa7724e00bae5ac54a6dbae16
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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