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

HRID 2357979Notes

Reaction equation

HRID 2357979 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]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:25])=[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:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:25])=[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 588368852,4-Dichloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

Product 1

HCID 588368794-(1-(but-3-enyl)hydrazinyl)-2-chloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.3 g (14.9 mmol) of 3-butenylhydrazine in 60 mL of THF was cooled to 0° C. and treated sequentially with 4.0 g (13.5 mmol) of 2,4-dichloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide 30 (Example 1, Step B) and 2.1 mL (14.9 mmol) of triethylamine. The resulting yellow slurry was warmed to room temperature and stirred for 23 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (75 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 17:3) to give the title compound. 1H-NMR (DMSO-d6) δ 2.24 (s, 6H), 2.40-2.48 (m, 2H), 3.32 (s, 2H), 3.80 (t, J=7.3 Hz, 2H), 5.03 (dd, J=10.3 Hz, 1.1 Hz, 1H), 5.13 (dd, J=17.2 Hz, 1.5 Hz, 1H), 5.75-5.86 (m, 1H), 7.07 (s, 3H), 8.15 (s, 1H), 9.61 (s, 1H). Mass Spectrum (ESI) m/e=346.1 (M+1).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (75 mL)
  2. extractionextracted with CH2Cl2 (3×100 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, 17:3)

Sources & evidence

ORD record
ord-d8cdd796d50b420c84dbe63cee48bf16
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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