Acetonitrile → 5-Trifluoromethyl-2-{4-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

HRID 657778Notes

Reaction equation

HRID 657778 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:12]3[CH2:20][NH:19][CH2:18][CH2:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][CH:4]=1.F[C:24]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:25]=1[C:26]#[N:27].C(#N)C.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:33][C:32]([F:34])([F:35])[C:29]1[CH:30]=[CH:31][C:24]([N:19]2[CH2:18][CH2:17][C:13]3[N:14]=[CH:15][N:16]=[C:11]([NH:10][CH2:9][C:6]4[CH:7]=[N:8][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:4][CH:5]=4)[C:12]=3[CH2:20]2)=[C:25]([CH:28]=1)[C:26]#[N:27]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrileHCID 59840682N-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 250618745-Trifluoromethyl-2-{4-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 2 mL microwave vial was charged with N-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (40 mg, 0.13 mmol), 2-fluoro-5-(trifluoromethyl)benzonitrile (150 mg, 0.78 mmol), acetonitrile (0.4 mL) and N,N-diisopropylethylamine (68 μL, 0.39 mmol). The mixture was subjected to microwave irradiation at 200° C. for 2 h. The mixture was diluted with chloroform (7 mL), and washed with 0.1 M NaH2PO4 (10 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column to yield a pale brown solid.

Workup

  1. customirradiation at 200° C. for 2 h
  2. washwashed with 0.1 M NaH2PO4 (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column
  7. customto yield a pale brown solid

Sources & evidence

ORD record
ord-4c8861b155554241bc290520e36967b8
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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