Diisopropylethylamine → (R)-6-(5-Methylpyridin-2-yl)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

HRID 241874Notes

Reaction equation

Cl.Cl.[F:3][C:4]([F:15])([F:14])[C:5]1[N:10]=[CH:9][C:8]([C@H:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]1[C:27]2[CH2:35][N:34]([C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][N:37]=3)[CH2:33][CH2:32][C:28]=2[N:29]=[CH:30][N:31]=1>C(#N)C>[CH3:42][C:39]1[CH:40]=[CH:41][C:36]([N:34]2[CH2:33][CH2:32][C:28]3[N:29]=[CH:30][N:31]=[C:26]([NH:13][C@@H:11]([C:8]4[CH:9]=[N:10][C:5]([C:4]([F:14])([F:3])[F:15])=[CH:6][CH:7]=4)[CH3:12])[C:27]=3[CH2:35]2)=[N:37][CH:38]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a stirred solution of (R)-1-(6-(trifluoromethyl)pyridin-3-yl)ethanamine dihydrochloride (44 mg, 0.17 mmol) and N,N-diisopropylethylamine (73 μL, 0.42 mmol) in acetonitrile (1.1 mL) was added 4-chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine (30 mg, 0.1 mmol). The reaction was capped and heated in the microwave for 10 hours at 180° C. The reaction mixture was quenched with excess water and allowed to stir for 10-15 minutes. The precipitated product was filtered, washed with water and dried in vacuum oven to obtain the title compound as a light tan solid.

Workup

customThe reaction was capped
customThe reaction mixture was quenched with excess water
filtrationThe precipitated product was filtered
washwashed with water
customdried in vacuum oven

Sources & evidence

ORD record: ord-e6359e973d454fa69a0de36c76424e3a
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653091B2

Reaction notes

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