Diisopropylethylamine → 5-Chloro-2-(4-((6-(dimethylamino)pyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657787Notes

Reaction equation

HRID 657787 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH3:11])[CH3:10])=[N:7][CH:8]=1.Br[C:13]1[C:14]2[CH2:22][N:21]([C:23]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:24]=3[C:25]#[N:26])[CH2:20][CH2:19][C:15]=2[N:16]=[CH:17][N:18]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:23]([N:21]2[CH2:20][CH2:19][C:15]3[N:16]=[CH:17][N:18]=[C:13]([NH:1][CH2:2][C:3]4[CH:8]=[N:7][C:6]([N:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=4)[C:14]=3[CH2:22]2)=[C:24]([CH:27]=1)[C:25]#[N:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167885965-(aminomethyl)-N,N-dimethylpyridin-2-amineHCID 598406952-(4-bromo-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-chlorobenzonitrile

Product 1

HCID 250624085-Chloro-2-(4-((6-(dimethylamino)pyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(aminomethyl)-N,N-dimethylpyridin-2-amine (24 mg, 0.16 mmol), 2-(4-bromo-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-chlorobenzonitrile (50 mg, 0.14 mmol), and N,N-diisopropylethylamine (62 μL, 0.36 mmol) in acetonitrile (1.9 mL) was subjected to microwave irradiation at 180° C. for 6 hrs. The reaction mixture was concentrated to an oil which was purified by silica gel column (0-15% MeOH/CH2Cl2) to obtain a light yellow solid.

Workup

  1. customirradiation at 180° C. for 6 hrs
  2. concentrationThe reaction mixture was concentrated to an oil which
  3. customwas purified by silica gel column (0-15% MeOH/CH2Cl2)
  4. customto obtain a light yellow solid

Sources & evidence

ORD record
ord-324ece2aa77e4e67ae7fe78254eca525
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

Loading…