Diisopropylethylamine → 5-Methyl-2-(4-(quinolin-7-ylmethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657823

Reaction equation

HRID 657823 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH2:31][NH2:32])[CH:29]=2)[CH:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:20][C:17]1[CH:18]=[CH:19][C:12]([N:10]2[CH2:9][CH2:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:32][CH2:31][C:28]4[CH:29]=[C:30]5[C:25]([CH:24]=[CH:23][CH:22]=[N:21]5)=[CH:26][CH:27]=4)[C:3]=3[CH2:11]2)=[C:13]([CH:16]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 17904490Quinolin-7-ylmethanamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 250613645-Methyl-2-(4-(quinolin-7-ylmethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (480 mg, 1.69 mmol) and quinolin-7-ylmethanamine (400 mg, 2.53 mmol) in acetonitrile (5 mL) and N,N-diisopropylethylamine (1.5 mL, 8.6 mmol) was subjected to microwave irradiation at 185° C. for 3.5 h. The reaction mixture was concentrated and the residue was purified by semi-prep HPLC (100×20.2 mm, C18 column; 30-60% acetonitrile-water [10 mM diethylamine]) to yield an off white solid.

Workup

  1. customirradiation at 185° C. for 3.5 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by semi-prep HPLC (100×20.2 mm, C18 column; 30-60% acetonitrile-water [10 mM diethylamine])
  4. customto yield an off white solid

Sources & evidence

ORD record
ord-2043df62de35492dbb24ffccc3572673
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Linked notes

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