Diisopropylethylamine → 5-Methyl-2-{4-[(R)-1-(2-methyl-pyrimidin-5-yl)-ethylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

HRID 657811Notes

Reaction equation

HRID 657811 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.[CH3:21][C:22]1[N:27]=[CH:26][C:25]([C@H:28]([NH2:30])[CH3:29])=[CH:24][N:23]=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:30][C@@H:28]([C:25]4[CH:24]=[N:23][C:22]([CH3:21])=[N:27][CH:26]=4)[CH3:29])[C:3]=3[CH2:11]2)=[C:13]([CH:16]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 250603295-Methyl-2-{4-[(R)-1-(2-methyl-pyrimidin-5-yl)-ethylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-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 (350 mg, 1.23 mmol) and (R)-1-(2-methylpyrimidin-5-yl)ethanamine (300 mg, 2.19 mmol) in acetonitrile (3 mL) and N,N-diisopropylethylamine (0.86 mL, 4.9 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-preparative HPLC (100×20.2 mm, C18 column; 30-55% acetonitrile-water [10 mM Et2NH]) 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-preparative HPLC (100×20.2 mm, C18 column; 30-55% acetonitrile-water [10 mM Et2NH])
  4. customto yield an off-white solid

Sources & evidence

ORD record
ord-f8a816ee39884af691d9d43a17d07d8a
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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