Hydrochloric Acid → N4-Ethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930655Notes

Reaction equation

[CH2:1]([N:3]([CH2:34][CH:35]1[CH2:39][CH2:38][CH2:37][O:36]1)[C:4]1[C:5]2[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])=[CH:13][CH:12]=2)[N:9]=1)[CH3:2].Cl>CO>[CH2:1]([N:3]([CH2:34][CH:35]1[CH2:39][CH2:38][CH2:37][O:36]1)[C:4]1[C:5]2[CH2:26][NH:25][CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])=[CH:15][CH:16]=2)[N:9]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (253 mg, 0.47 mmol) was dissolved in methanol (3 mL). Hydrochloric acid (0.017 mL, 0.47 mmol) was added and the reaction mixture was stirred at 80° C. for 1 h. The solvent was evaporated and the crude N4-ethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (190 mg, 92%) was used as such in the next step. MS (ES+) m/z 434.3 (M+H)+

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-7c812390d8b44d22b1f5f1838f66c638
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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