Diisopropylethylamine → HCID 53251678, compound

HRID 473414Notes

Reaction equation

HRID 473414 reaction equation
[C:1]1([C:7]2[C:8]([CH:17]([NH2:19])[CH3:18])=[N:9][C:10]3[C:15]([CH:16]=2)=[N:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[C:25](Cl)[N:24]=[CH:23][N:22]=1.CCN(C(C)C)C(C)C>CCCCO>[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[C:25]([NH:19][CH:17]([C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][N:14]=3)[N:9]=2)[CH3:18])[N:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 58318606HCID 58318606, compound

Product 1

HCID 53251678HCID 53251678, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-(3-Phenyl-1,5-naphthyridin-2-yl)ethanamine (46 mg, 0.19 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (28.5 mg, 1.0 eq) and Hunig's base (39 μL, 1.2 eq) in n-BuOH (2 mL) was heated to 130° C. for 4 h. The mixture was cooled to rt, filtered and washed with small amount of EtOH to give a white solid as 4-amino-6-(1-(3-phenyl-1,5-naphthyridin-2-yl)ethylamino)pyrimidine-5-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (1H, dd, J=8.0, 4.0 Hz), 8.44 (1H, dd, J=8.0, 4.0 Hz), 8.21 (1H, s), 7.97 (1H, s), 7.84 (1H, dd, J=8.0, 4.0 Hz), 7.61-7.47 (6H, m), 7.30 (1H, br, s), 5.63 (1H, t, J=8.0 Hz)), 1.31 (3H, d, J=8.0 Hz); LC-MS (ESI) m/z 368 [M+H]+.

Workup

  1. filtrationfiltered
  2. washwashed with small amount of EtOH

Sources & evidence

ORD record
ord-fb5d13fb8d9c4d3c8cd8945ee37b7178
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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