Hydrochloric Acid → HCID 178423313, compound

HRID 635702Notes

Reaction equation

HRID 635702 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][CH:12]([CH3:14])[CH2:11][CH:10]([C:15]3[NH:20][C:19]4=[CH:21][CH:22]=[N:23][C:18]4=[CH:17][N:16]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CC[O:26]C(C)=O.[ClH:30]>CO>[OH2:26].[ClH:30].[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][CH:12]([CH3:14])[CH2:11][CH:10]([C:15]3[NH:20][C:19]4=[CH:21][CH:22]=[N:23][C:18]4=[CH:17][N:16]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423312HCID 178423312, compound

Product 1

HCID 178423313HCID 178423313, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing [1-(3-fluorophenyl)vinyl]pyrrolidine (freshly prepared before use) (1.10 g, 5.81 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.21 g, 5.81 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (0.9 mL, 5.81 mmol), piperidine (Aldrich Chemical Company) (0.9 mL, 9.3 mmol), NEt3 (Aldrich Chemical Company) (1.0 mL) and SnCl2 (Aldrich Chemical Company) (17 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 82 mg (5%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.65 (br s, 4), 2.42 (s, 3), 3.72 (br s, 4), 6.85 (s, 1), 7.22 (m, 1), 7.51 (m, 1), 7.75-7.81 (m, 2), 10.97 (s, 1). MS m/z: 311 (M+1). To a hot (near boiling) solution of 6-(3-fluorophenyl)-2-methyl-4-piperidylpyrrolo[3,2-d]pyrimidine (82.0 mg, 0.26 mmol) in 10:1 EtOAc: MeOH (30 mL) was added 1M etheral HCl (Aldrich Chemical Company) (265 mL, 0.26 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (2×5 mL) and dried under vacuum to give 82 mg (91%) of the title compound as beige colored small needles. Mp: >285° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 2.57 (s, 3), 4.06 (br s, 4), 6.99 (s, 1), 7.35 (t, 1, J=8.5), 7.60 (q, 1, J=7.7), 7.83 (d, 1, J=7.6), 7.91 (d, 1, J=10.2), 11.99 (s, 1), 14.34 (s, 1). MS m/z: 311 (M+1). Anal. Calcd for C18H19FN4.HCl.H2O: C, 59.17; H, 6.09; N, 15.34; Cl, 9.70. Found C, 59.17; H, 6.09; N, 15.21; Cl, 9.81.

Workup

  1. customCrystallization
  2. temperaturecooled
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with Et2O (2×5 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3b3c4f83192b4de9a8caa0ce6f42421b
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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