Hydrochloric Acid → N-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)-4-(1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 1930638Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH3:32])[C:17]4[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.Cl>CO>[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[N:15]=[C:16]([CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH3:32])[C:17]4[CH2:23][NH:22][CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:11][CH:12]=2)[CH:4]=[CH:5][N:6]=1

Participants

Conditions

Temperature: 75 °C

Procedure

tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-(1-phenylethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (612 mg, 1.20 mmol) was dissolved in methanol (10 mL). Hydrochloric acid (0.098 mL, 1.20 mmol) was added and the reaction mixture was stirred at 75° C. for 1 h. The solvent was evaporated under reduced pressure and the crude N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-4-(1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (490 mg, 100%) was used as such in the subsequent step. MS (ES+) m/z 411 (M+H)+

Workup

customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-951e24f833b846e688e0f7339c9595db
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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