Dimethylformamide dimethyl acetal → HCID 69230482, compound

HRID 628824Notes

Reaction equation

HRID 628824 reaction equation
[C:1](C1C=CC(C(OC)=O)=CC=1)(=O)[CH3:2].COC(OC)N(C)C.CN(C)[CH:24]=[CH:25][C:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)=O.[CH:38]([C:41]1[CH:49]=[CH:48][C:44]([C:45]([NH2:47])=[NH:46])=[CH:43][CH:42]=1)([CH3:40])[CH3:39]>C(O)C>[CH:38]([C:41]1[CH:49]=[CH:48][C:44]([C:45]2[N:47]=[C:26]([C:28]3[CH:36]=[CH:35][C:31]([C:32]([O:34][CH2:1][CH3:2])=[O:33])=[CH:30][CH:29]=3)[CH:25]=[CH:24][N:46]=2)=[CH:43][CH:42]=1)([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 78373Dimethylformamide dimethyl acetalHCID 137990Methyl 4-acetylbenzoateHCID 65387334-IsopropylbenzamidineHCID 69232310HCID 69232310, compound

Product 1

HCID 69230482HCID 69230482, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Part A. A solution of methyl 4-acetylbenzoate (1.00 g, 5.61 mmol) and dimethylformamide dimethyl acetal (746 μL, 5.61 mmol) in ethanol (5 mL) is heated to reflux for 12 h. The solution is cooled and evaporated, and the residue is separated by column chromatography to afford the product as a mixture of methyl and ethyl esters of 4-(3-dimethylamino-acryloyl)benzoic acid (679 mg). A portion of this material (121 mg) is dissolved in ethanol (5 mL) and treated with 4-isopropyl-benzamidine (81 mg). The solution is heated to reflux for 12 h., cooled, filtered through celite, and evaporated. The residue is separated by column chromatography (silica gel, 1:4 ethyl acetate-hexane) to afford the product, ethyl 4-[2-(4-isopropyl-phenyl)-pyrimidin-4-yl]-benzoate.

Workup

  1. temperatureto reflux for 12 h
  2. temperatureThe solution is cooled
  3. customevaporated
  4. customthe residue is separated by column chromatography
  5. customto afford the product
  6. temperatureThe solution is heated
  7. temperatureto reflux for 12 h.
  8. temperaturecooled
  9. filtrationfiltered through celite
  10. customevaporated
  11. customThe residue is separated by column chromatography (silica gel, 1:4 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ee76f39cf11b4baaae59b9fcae1086a8
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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