2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(2-(4-(diethylamino)phenyl)thiazol-5-yl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56113Notes

Reaction equation

HRID 56113 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([NH2:15])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:2].C[Al](C)C.[NH:22](/[C:26](/[CH3:32])=[CH:27]\[C:28](OC)=[O:29])[C:23]([CH3:25])=O>C(Cl)Cl>[CH2:16]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([N:15]3[C:28](=[O:29])[CH:27]=[C:26]([CH3:32])[N:22]=[C:23]3[CH3:25])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:17]

Participants

5

Reactant 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 900236882-(4-(Diethylamino)phenyl)thiazol-5-amine

Product 1

HCID 729483993-(2-(4-(diethylamino)phenyl)thiazol-5-yl)-2,6-dimethylpyrimidin-4(3H)-oneYield 3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-(diethylamino)phenyl)thiazol-5-amine (0.45 g, 1.82 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (4.5 mL, 9.0 mmol, 2 M in toluene) dropwise at rt. The reaction mixture was stirred at rt for 1 h, followed by the addition of a solution of methyl 3-acetaminocrotonate ((315 mg, 2 mmol) in anhydrous CH2Cl2 (5 mL). The reaction mixture was stirred at rt for 3 days, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography to give the title compound as a yellow solid (22 mg, 3%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringThe reaction mixture was stirred at rt for 3 days
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-650e4b4099824ab0b6fc307be33627cd
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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