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

HRID 657805Notes

Reaction equation

HRID 657805 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:20][CH2:19][C:13]3[N:14]=[CH:15][N:16]=[C:17](Cl)[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26]([C@H:29]([NH2:31])[CH3:30])=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:20][CH2:19][C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH:31][C@@H:29]([C:26]4[CH:25]=[N:24][C:23]([O:22][CH3:21])=[N:28][CH:27]=4)[CH3:30])[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 598406875-Chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrileHCID 59840707(R)-1-(2-methoxypyrimidin-5-yl)ethanamine

Product 1

HCID 598407015-Chloro-2-{4-[(R)-1-(2-methoxy-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 5-chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile (130 mg, 0.41 mmol) and (R)-1-(2-methoxypyrimidin-5-yl)ethanamine (85 mg, 0.55 mmol) (prepared similarly according to the method for Intermediate 16) in acetonitrile (3 mL) and N,N-diisopropylethylamine (140 μL, 0.83 mmol) was subjected to microwave irradiation at 180° C. for 3 h. The reaction mixture was concentrated and the residue was purified by semi-preparative HPLC (100×20.2 mm, C18 column; 30-60% acetonitrile-water [10 mM Et2NH]) to yield a white solid.

Workup

  1. customprepared similarly
  2. customirradiation at 180° C. for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by semi-preparative HPLC (100×20.2 mm, C18 column; 30-60% acetonitrile-water [10 mM Et2NH])
  5. customto yield a white solid

Sources & evidence

ORD record
ord-a9170558f5e64346b24ca99ef2c00ab4
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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