Hydrochloric Acid → 5-(4-chloro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HCl
Reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[C:12]([Cl:27])=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)=[CH:9][N:8]([CH3:28])[C:4]=2[N:5]=[CH:6][N:7]=1.[ClH:29]>>[ClH:27].[ClH:29].[Cl:27][C:12]1[C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH3:28])[CH:9]=2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][NH:16]2Participants
3
Procedure
A suspension of 1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-4-chloro-2,3-dihydro-1H-indole-1-carboxylate (0.716 g, 1.791 mmol) in HCl (4 M, dioxane) (30 mL, 120 mmol) was stirred at room temperature overnight. LCMS indicated good conversion. The reaction mixture was concentrated to afford 5-(4-chloro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HCl (667 mg, 1.790 mmol, 100% yield) as an off-white solid. LC-MS (ES) m/z=300 [M+H]+. 1H NMR (400 MHz, DMSO-d6) d ppm 3.05 (t, J=8.59 Hz, 2H), 3.56-3.63 (m, 2H), 3.81-3.98 (m, 8H), 6.55-6.62 (m, 1H), 7.01 (d, J=7.58 Hz, 1H), 7.49 (s, 1H), 8.45 (s, 1H).