Triethylamine → 4-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide

HRID 2357991Notes

Reaction equation

HRID 2357991 reaction equation
[CH2:1]([NH:5][NH2:6])[CH2:2][CH:3]=[CH2:4].[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]([C:15]([NH:17][C:18]2[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:25])=[O:16])=[CH:10][N:9]=1.C(N(CC)CC)C>C1COCC1>[CH2:1]([N:5]([C:12]1[C:11]([C:15]([NH:17][C:18]2[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][C:23]=2[Cl:24])=[O:16])=[CH:10][N:9]=[C:8]([Cl:7])[N:13]=1)[NH2:6])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20337519HCID 20337519, compoundHCID 729421582,4-Dichloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide

Product 1

HCID 588368804-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 230 mg (2.7 mmol) of 3-butenylhydrazine in 10.5 mL of THF was cooled to 0° C. and treated sequentially with 800 mg (2.4 mmol) of 2,4-dichloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide and 370 μl (2.6 mmol) of triethylamine. The resulting yellow slurry was warmed to room temperature and stirred for 25 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 99.5:0.5) to give the title compound 85. 1H-NMR (DMSO-d6) δ 3.17 (d, J=5.2 Hz, 2H), 3.31 (s, 2H), 3.80 (t, J=7.3 Hz, 2H), 5.04 (d, J=10.3 Hz, 1H), 5.13 (d, J=17.1 Hz, 1H), 5.77-5.88 (m, 1H), 7.35 (t, J=8.3 Hz, 1H), 7.55 (d, J=8.2 Hz, 2H), 8.15 (s, 1H), 10.19 (s, 1H). Mass Spectrum (ESI) m/e=385.9 (M+1).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 99.5:0.5)

Sources & evidence

ORD record
ord-d9053b8dfab24a2f8d307a3722492d79
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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