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

HRID 241875Notes

Reaction equation

HRID 241875 reaction equation
Br[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=3)[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[N:26]=[CH:25][C:24]([C@@H:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.C(#N)C>C(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH2:9][CH2:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:29][C@H:27]([C:24]4[CH:25]=[N:26][C:21]([C:20]([F:31])([F:19])[F:30])=[CH:22][CH:23]=4)[CH3:28])[C:3]=3[CH2:11]2)=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 581035754-Bromo-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidineHCID 58103579(alphaS)-alpha-Methyl-6-(trifluoromethyl)-3-pyridinemethanamine

Product 1

HCID 25033575(S)-6-(5-Chloropyridin-2-yl)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amineYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (25 mg, 0.077 mmol), (S)-1-(6-(trifluoromethyl)pyridin-3-yl)ethanamine (73.0 mg, 0.384 mmol), N,N-diisopropylethylamine (40.1 μL, 0.230 mmol), and acetonitrile (1.0 mL) were added to a 0.5 to 2 mL microwave vial. The mixture was reacted in the microwave reactor for 2.5 hrs at 200° C. The resulting mixture was treated with CH2Cl2 and washed with 1 M NaH2PO4, dried (Na2SO4), and evaporated. The residue was purified by silica gel column to obtain a light yellow solid (18.6 mg).

Workup

  1. customThe mixture was reacted in the microwave reactor for 2.5 hrs at 200° C
  2. washwashed with 1 M NaH2PO4
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-57a1ec5796414503a141b219a3cc77ef
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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