4-Amino-2,6-dichloropyridine → 2-(2,6-Dichloropyridin-4-ylamino)-6-(3-acetamidophenyl)-pyrazine

HRID 16263

Reaction equation

HRID 16263 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Cl:18][C:19]1[CH:24]=[C:23]([NH2:25])[CH:22]=[C:21]([Cl:26])[N:20]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[C:23]([NH:25][C:13]2[N:12]=[C:11]([C:7]3[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=3)[CH:16]=[N:15][CH:14]=2)[CH:22]=[C:21]([Cl:26])[N:20]=1

Participants

6

Reactant 4

HCID 1376524-Amino-2,6-dichloropyridineHCID 634876Binap, (A+-)-HCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 115236392-(2,6-Dichloropyridin-4-ylamino)-6-(3-acetamidophenyl)-pyrazineYield 7.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using Method L, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 2,6-dichloropyridin-4-amine (57.1 mg, 0.35 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 85° C. for 16 hours. The same workup as for Method L followed by preparative TLC afforded 7 mg of title compound. Yield: 7.8%. 1H NMR (250 MHz, DMSO-d6) δ 2.08 (s, 3 H), 7.48 (t, 1 H, 7.9 Hz), 7.65 (d, 1 H, 8.0 Hz), 7.71 (d, 1 H, 7.6 Hz), 7.85 (s, 2 H), 8.30 (s, 1 H), 8.32 (bs, 1 H), 8.66 (s, 1 H), 10.10 (s, 1 H), 10.55 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 23.9, 110.3, 117.47, 120.6, 121.2, 129.4, 133.4, 134.2, 136.3, 140.0, 148.3, 149.5, 149.7, 151.4, 168.3; m/z 374.1 [(M+H)+, calcd for C17H13Cl2N5O 373.0].

Workup

  1. customwere reacted at 85° C. for 16 hours

Sources & evidence

ORD record
ord-f702c664599b4125b288cb1d3dfb61c1
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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