Triethylamine → 1-(4-Methylpiperazin-1-yl)-7-(pyrimid-5-yl)naphthalene

HRID 235153Notes

Reaction equation

HRID 235153 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:9][CH:8]=1)(=O)=O.C[Sn](C)(C)[C:28]1[CH:29]=[N:30][CH:31]=[N:32][CH:33]=1.C(N(CC)CC)C.[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>CN(C)C=O>[CH3:23][N:20]1[CH2:21][CH2:22][N:17]([C:14]2[C:15]3[C:10](=[CH:9][CH:8]=[C:7]([C:28]4[CH:29]=[N:30][CH:31]=[N:32][CH:33]=4)[CH:16]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:18][CH2:19]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 127998215-Trimethylstannyl-pyrimidineHCID 22115665HCID 22115665, compound

Product 1

HCID 233535421-(4-Methylpiperazin-1-yl)-7-(pyrimid-5-yl)naphthaleneYield 29.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-trifluoromethylsulfonyloxy-1-(4-methylpiperazin-1-yl)naphthalene (0.250 g, 0.67 mmol), bis(triphenylphosphine)palladium[11]chloride (0.025 g, 0.036 mmol), 5-trimethylstannylpyrimidine (0.178 g, 0.74 mmol, from Preparation 6), triethylamine (0.45 mL, 3.23 mmol), lithium chloride (0.088 g, 2.07 mmol), 2,6-di-tert-butyl-4-methylphenol (approximately 0.01 g), and N, N-dimethylformamide (12.5 mL) was heated between 100° C. to 115° C. under nitrogen for 45 minutes. The resulting mixture was concentrated via evaporation under reduced pressure, and the residue was column chromatographed using silica gel (approximately 25 g) and elution with 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]to afford the title compound (0.060 g, 0.20 mmol, 29%) as a pale yellow foam: Rf =0.15 in 20% methanol in ethyl acetate; 13C NMR (CDCl3) δ 157.3, 155.0, 149.8, 134.6, 134.5, 130.8, 129.9, 129.0, 127.1, 124.0, 123.4, 122.1, 116.0, 55.4, 52.7, 45.9; LRMS (m/z, relative intensity) 304 (M+, 7), 240 (100), 225 (15), 196 (16), 169 (44), 155 (33), 141 (16); HRMS m/e calculated for C19H20N4 304.1690. Observed m/e 304.1689.

Workup

  1. temperaturewas heated between 100° C. to 115° C. under nitrogen for 45 minutes
  2. concentrationThe resulting mixture was concentrated via evaporation under reduced pressure
  3. customchromatographed
  4. washsilica gel (approximately 25 g) and elution with 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]

Sources & evidence

ORD record
ord-80ad58a063ef4654a3296e1b853d0f25
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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