Hydrochloric Acid → HCID 178473895, compound

HRID 635765Notes

Reaction equation

HRID 635765 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].Cl>CCOC(C)=O>[ClH:1].[C:18]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[N:7]=[C:6]([CH3:8])[NH:5][C:4]3[C:3]=2[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=3)[CH2:23][CH2:22]1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 837951-AcetylpiperazineHCID 178432852HCID 178432852, compound

Product 1

HCID 178473895HCID 178473895, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask was added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (500 mg, 2.05 mmol) and 1-acetyl-piperazine (Aldrich Chemical Company) (525 mg, 4.10 mmol). The flask was purged with N2 and the mixture was heated to 180° C. for 30 min. The reaction was allowed to cool to room temperature and the crude material was purified by flash chromatography on silica gel with 10% MeOH/EtOAc as eluant to give 600 mg (87% yield) of an off white solid. The free base (400 mg, 1.2 mmol) was dissolved in hot EtOAc (10 mL) and anhydrous ethereal HCl (1.2 mL, of a 1.0 M soln, 1.2 mmol) was added dropwise. The mixture was stirred for 2 h and allowed to cool to room temperature. The resulting solid was filtered and dried under high vacuum to give 205 mg (96% yield) of the title compound as a light yellow solid. Mp: 282-283° C. 1H NMR (DMSO-d6; 400 MHz): d 2.09 (s, 3), 2.61 (s, 3), 3.7 (s, 4), 4.14 (dt, J=5.3, 14), 6.95 (s, 1), 7.54 (m, 3), 8.00 (d, 2, J=6.88). MS m/z: 366 (M+1); 364 (M−1). Anal. Calcd for C19H21N5O.HCl.: C, 60.76; H, 5.95; N, 18.65; O, 4.45; Cl, 10.19. Found: C, 60.76; H, 5.90; N, 18.64; Cl, 10.15.

Workup

  1. customThe flask was purged with N2
  2. temperatureto cool to room temperature
  3. customthe crude material was purified by flash chromatography on silica gel with 10% MeOH/EtOAc as eluant
  4. customto give 600 mg (87% yield) of an off white solid
  5. temperatureto cool to room temperature
  6. filtrationThe resulting solid was filtered
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-46343fda0c344de7aca044b94a5a4281
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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