Triethylamine → (S)-3-(1-(2,5-dichloropyrimidin-4-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

HRID 1046766Notes

Reaction equation

HRID 1046766 reaction equation
[NH2:1][C@H](C1N(C2C=CC=CC=2)C(=O)C2C(C=1)=CC=CC=2C)C.ClC1N=C(Cl)C(Cl)=CN=1.C(N(CC)CC)C.[Cl:38][C:39]1[N:44]=[C:43]([NH:45][C@H:46]([C:48]2[N:49]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:50](=[O:59])[C:51]3[C:56]([CH:57]=2)=[CH:55][CH:54]=[CH:53][C:52]=3[CH3:58])[CH3:47])[C:42]([Cl:66])=[CH:41][N:40]=1>CCCCO>[NH2:1][C:39]1[N:44]=[C:43]([NH:45][C@H:46]([C:48]2[N:49]([C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:50](=[O:59])[C:51]3[C:56]([CH:57]=2)=[CH:55][CH:54]=[CH:53][C:52]=3[CH3:58])[CH3:47])[C:42]([Cl:66])=[CH:41][N:40]=1.[Cl:38][C:39]1[N:44]=[C:43]([NH:45][C@H:46]([C:48]2[N:49]([C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:50](=[O:59])[C:51]3[C:56]([CH:57]=2)=[CH:55][CH:54]=[CH:53][C:52]=3[CH3:58])[CH3:47])[C:42]([Cl:66])=[CH:41][N:40]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 58008742(S)-3-(1-(2,5-dichloropyrimidin-4-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneHCID 58008747(S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one2×

Product 2

HCID 58008735(S)-3-(1-(2-amino-5-chloropyrimidin-4-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneHCID 58008742(S)-3-(1-(2,5-dichloropyrimidin-4-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneYield 74%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (150 mg, 0.54 mmol), 2,4,5-trichloropyrimidine (119 mg, 0.65 mmol) and triethylamine (137 mg, 1.35 mmol) in n-BuOH (10 mL) was stirred at reflux for 2 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (MeOH:CH2Cl2=1:100) to afford the desired product, (S)-3-(1-(2,5-dichloropyrimidin-4-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (2H)-one (compound 5101) (170 mg, 74% yield) as a white solid.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (MeOH:CH2Cl2=1:100)

Sources & evidence

ORD record
ord-40d451f4dc6742a5b2f44d045cb9c0ee
Source dataset
uspto-grants-2013_10
Patent number
US08569323B2

Reaction notes

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