Diisopropylethylamine → (S)-2-(4-(2-(tert-butyldimethylsilyloxy)-1-(2-methylpyrimidin-5-yl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-chlorobenzonitrile

HRID 657813Notes

Reaction equation

HRID 657813 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].[Si:21]([O:28][CH2:29][C@H:30]([C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[N:36][CH:37]=1)[NH2:31])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)C(C)C)(C)C>C(#N)C>[Si:21]([O:28][CH2:29][C@@H:30]([NH:31][C:17]1[C:12]2[CH2:11][N:10]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=3[C:7]#[N:8])[CH2:20][CH2:19][C:13]=2[N:14]=[CH:15][N:16]=1)[C:32]1[CH:37]=[N:36][C:35]([CH3:38])=[N:34][CH:33]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 598406875-Chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrileHCID 67053779(S)-2-(tert-butyldimethylsilyloxy)-1-(2-methylpyrimidin-5-yl)ethanamine

Product 1

HCID 69177698(S)-2-(4-(2-(tert-butyldimethylsilyloxy)-1-(2-methylpyrimidin-5-yl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-chlorobenzonitrile

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 (150 mg, 0.49 mmol) and (S)-2-(tert-butyldimethylsilyloxy)-1-(2-methylpyrimidin-5-yl)ethanamine (144 mg, 0.54 mmol) in acetonitrile (2 mL) and N,N-diisopropylethylamine (0.5 mL, 3 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 to yield the product as a yellow 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

Sources & evidence

ORD record
ord-d8c53f8e8f28465f8fe4064cb674b559
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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