Sodium Sulfate → HCID 68405926, compound

HRID 2244443Notes

Reaction equation

HRID 2244443 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C[Al](C)C.C([O:15][C:16]([C:18]1[N:19]=[C:20]([CH3:35])[S:21][C:22]=1[N:23]([C:28]([O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1)=[O:29])[CH2:24][CH:25]1[CH2:27][CH2:26]1)=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.O>[CH:32]1([CH2:31][O:30][C:28](=[O:29])[N:23]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:22]2[S:21][C:20]([CH3:35])=[N:19][C:18]=2[C:16](=[O:15])[NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=2)[CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 2957632-Methylpyrimidin-4-amineHCID 16682925TrimethylaluminumHCID 68406634HCID 68406634, compound

Product 1

HCID 68405926HCID 68405926, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-methyl-4-amino-pyrimidine (0.184 g, 1.68 mmol) in 10 ml dry dioxane was treated at 0° C. with trimethylaluminium (2M in hexane, 0.84 ml, 1.68 mmol). The mixture was stirred at room temperature for 1 h. 5-(Cyclopropylmethoxycarbonyl-(cyclopropylmethyl)-amino)-2-methyl-thiazole-4-carboxylic acid ethyl ester (0.135 g, 0.40 mmol) was added and the reaction mixture was refluxed for 4 h. 1 ml water and 2 g sodium sulfate were sequentially added and filtered. The filtrate was evaporated and the residue purified by flash chromatography with heptane/ethyl acetate 100:0→0:100 gradient to yield cyclopropylmethyl-[2-methyl-4-(2-methyl-pyrimidin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid cyclopropylmethyl ester (0.101 g, 63%) as a colourless oil, MS (ISP): m/e=402.5 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified by flash chromatography with heptane/ethyl acetate 100:0→0:100 gradient

Sources & evidence

ORD record
ord-c4dfdf30bc574ba7afc6e8edad56994c
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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