Potassium Carbonate → HCID 178433065, compound

HRID 1371136Notes

Reaction equation

Cl[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.[CH3:18][CH:19]1[CH2:23][CH2:22][CH2:21][NH:20]1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:8][C:6]1[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]2=[C:2]([N:20]2[CH2:21][CH2:22][CH2:23][CH:19]2[CH3:18])[N:7]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (230 mg, 0.94 mmol), 2-methylpyrrolidine (Alfa) (799 mg, 9.4 mmol), K2CO3 (650 mg, 4.7 mmol) in H2O (1.5 mL) was stirred at 105° C. for 20 h. Upon cooling to room temperature, the reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (3×15 mL). The organic phase was washed with H2O (20 mL), saturated NaCl (20 mL), dried over Na2SO4, and concentrated with a rotary evaporator. Chromatography on silica gel with a gradient eluant of MeOH (0-10%):CH2Cl2 (100-90%) afforded 250 mg (93%) of the title compound as an off-white solid. Mp: 219-221° C. 1H NMR (CDCl3; 400 MHz): δ 1.39 (d, 3, J=6.3), 1.79 (m, 1), 2.22-2.07 (m, 3), 2.58 (s, 3), 3.90 (m, 1), 4.04 (m, 1), 4.59 (m, 1), 6.74 (s, 1), 7.38 (t, 1, J=7.4), 7.46 (t, 2, J=7.4), 7.63 (d, 2, J=7.4), 8.31 (s, 1). MS m/z: 293 (M+1), 291 (M−1). HRMS: Calcd for M+H: 293.1766. Found: 293.1770.

Workup

temperatureUpon cooling to room temperature
extractionextracted with EtOAc (3×15 mL)
washThe organic phase was washed with H2O (20 mL), saturated NaCl (20 mL)
dry with materialdried over Na2SO4
concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record: ord-8c02ae2501e140e2bcc701eb5a281a23
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583154B1

Reaction notes

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