Hydrochloric Acid → HCID 178479623, compound

HRID 635691Notes

Reaction equation

HRID 635691 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[O:20][C:19]5[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=5[CH:17]=4)=[N:15][C:10]3=[CH:9][N:8]=2)[CH2:3][CH2:2]1.CCOC(C)=O.[ClH:31]>CO>[OH2:20].[ClH:31].[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:12][C:11]3=[CH:13][C:14]([C:16]4[O:20][C:19]5[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=5[CH: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 178420018HCID 178420018, compound

Product 1

HCID 178479623HCID 178479623, compoundYield 171%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl) benzo[b]furan (freshly prepared before use) (2.29 g, 10.7 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.10 g, 10.7 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.9 mL, 10.7 mmol), piperidine (Aldrich Chemical Company) (1.7 mL, 17.1 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (32 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 612 mg (18%) of the free base as a tan colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.68 (s, 6), 3.77 (s, 4), 6.94 (s, 1), 7.32 (d, 2, J=18.9), 7.68 (t, 3, J=26.3), 8.28 (s, 1), 11.54 (s, 1). MS m/z: 319 (M+1). To a hot solution of 2-(4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzo[b]furan (0.61 g, 1.92 mmol) in 3:1 EtOAc: MeOH (50 mL) was added 1M etheral HCl (Aldrich Chemical Company) (1.90 mL, 1.92 mmol). Upon cooling crystalliztion occurred and the solid was collected by filtration. Thsi material was washed with Et2O (2×10 mL) and dried under vacuum to give 612 mg (90%) of the title compound as a brown colored solid. Mp: 278.5-281° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.74 (s, 6), 4.10 (s, 4), 7.09 (s, 1), 7.36 (t, 1, J=7.5), 7.45 (t, 1, J=7.9), 7.72 (d, 1, J=8.3), 7.80 (d, 1, J=7.7), 7.93 (s, 1), 8.64 (s, 1), 12.76 (s, 1), 14.66 (s, 1). MS M/z : 319 (M+1). Anal. Calcd for C19H18N4O.HCl.0.5H2O: C, 62.80; H, 5.41; N, 15.42; Cl, 9.76. Found C, 62.89; H, 5.46; N, 15.36; Cl, 9.89.

Workup

  1. temperatureUpon cooling crystalliztion
  2. filtrationthe solid was collected by filtration
  3. washThsi material was washed with Et2O (2×10 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7b48edf28e0940d2b34f2a1861c7feaa
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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