Water → [6-(5-Chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yl]-[(R)-cyclopropyl-(6-trifluoromethyl-pyridin-3-yl)-methyl]-amine

HRID 241877Notes

Reaction equation

Cl.Cl.[CH:3]1([C@H:6]([C:8]2[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[NH2:7])[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.Br[C:28]1[C:29]2[CH2:37][N:36]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][N:39]=3)[CH2:35][CH2:34][C:30]=2[N:31]=[CH:32][N:33]=1.O>C(#N)C>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([N:36]2[CH2:35][CH2:34][C:30]3[N:31]=[CH:32][N:33]=[C:28]([NH:7][C@H:6]([CH:3]4[CH2:5][CH2:4]4)[C:8]4[CH:9]=[N:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=4)[C:29]=3[CH2:37]2)=[N:39][CH:40]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a stirred solution of (R)-cyclopropyl(6-(trifluoromethyl)pyridin-3-yl)methanamine dihydrochloride (53 mg, 0.184 mmol) and N,N-diisopropylethylamine (60 uL, 0.4 mmol) in acetonitrile (1.2 mL) was added 4-bromo-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (30 mg, 0.092 mmol). The reaction mixture was heated in microwave reactor at 180° C. for 8 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated to obtain a brown oil which was purified using HPLC (semi-prep 30-80% water/acetonitrile) to give a light brown solid (13 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialdried (MgSO4)
concentrationconcentrated
customto obtain a brown oil which
customwas purified

Sources & evidence

ORD record: ord-5093e4ffc178454aa5fcbc39e354989b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653091B2

Reaction notes

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