Hydrochloric Acid → HCID 178423324, compound

HRID 1371151Notes

Reaction equation

HRID 1371151 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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=[C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423323HCID 178423323, compound

Product 1

HCID 178423324HCID 178423324, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing (1,2-diphenylvinyl)pyrrolidine (freshly prepared before use) (1.83 g, 7.35 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.50 g, 7.35 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.3 mL, 7.35 mmol), piperidine (1.2 mL, 11.8 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (Aldrich Chemical Company) (22 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 110 mg (4%) of the free base as a pale yellow colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.65 (br s, 6), 2.42 (s, 3), 3.72 (br s, 4), 7.19 (m, 1), 7.28 (m, 2), 7.39-7.44 (m, 7), 11.20 (s, 1). MS m/z: 369 (M+1). To a solution of 2-methyl-6,7-diphenyl-4-piperidylpyrrolo[3,2-d]pyrimidine (148 g, 0.40 mmol) in 1:1 EtOAc:MeOH (50 mL) was added 1M etheral HCl (Aldrich Chemical Company) (400 mL, 0.40 mmol). The solvent was removed under reduced pressure and then dried under vacuum to give 83 mg (51%) of the title compound as a beige colored solid. Mp: 169-171° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.72 (br s, 6), 2.56 (s, 3), 4.06 (br s, 4), 7.29 (dd, 2, J=1.7, 6.0), 7.37-7.45 (m, 8), 12.26 (s, 1), 13.40 (s, 1). MS m/z: 369 (M+1). Anal. Calcd. for C24H24N4.HCl.H2O: C, 68.25; H, 6.40; N, 13.27; Cl, 8.29. Found C, 68.33; H, 6.41; N, 13.15; Cl, 8.50.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried under vacuum

Sources & evidence

ORD record
ord-c39f4ed720324fae8c4201c18066b153
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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