Acetonitrile → 5-Bromo-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657792Notes

Reaction equation

HRID 657792 reaction equation
[CH3:1][O:2][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.[Br:21][C:22]1[CH:23]=[CH:24][C:25](F)=[C:26]([CH:29]=1)[C:27]#[N:28].C(N(CC)C(C)C)(C)C.C(#N)C>CCOC(C)=O>[Br:21][C:22]1[CH:23]=[CH:24][C:25]([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]([O:2][CH3:1])=[CH:4][CH:5]=4)[C:12]=3[CH2:20]2)=[C:26]([CH:29]=1)[C:27]#[N:28]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 27249005-Bromo-2-fluorobenzonitrile2×HCID 59840689N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 250624105-Bromo-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (350 mg, 1.3 mmol), 5-bromo-2-fluorobenzonitrile (640 mg, 3.2 mmol), N,N-diisopropylethylamine (0.67 mL, 3.9 mmol), and acetonitrile (4 mL) was subjected to microwave irradiation at 180° C. for 3 h. After that additional 5-bromo-2-fluorobenzonitrile (450 mg) was added and the mixture was subjected to microwave irradiation at 180° C. for another 2 h. After cooling, the mixture was diluted with EtOAc (100 mL) and washed with aq. Na2CO3 solution and brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column (EtOAc: 100%) to yield a light yellow solid.

Workup

  1. customirradiation at 180° C. for 3 h
  2. customirradiation at 180° C. for another 2 h
  3. temperatureAfter cooling
  4. washwashed with aq. Na2CO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column (EtOAc: 100%)
  8. customto yield a light yellow solid

Sources & evidence

ORD record
ord-e10d8c0141c94fe681cc34389ae6324e
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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