Sulfuric acid magnesium salt (1:1) → HCID 67387982, compound

HRID 1958335Notes

Reaction equation

HRID 1958335 reaction equation
C[Al](C)C.[C:5]1([C:11]2[N:12]=[C:13]3[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]3[CH:20]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O:23][C:24]([C:26]1[C:27]([NH:32][C:33]2[CH:34]=[N:35][CH:36]=[N:37][CH:38]=2)=[N:28][N:29]([CH3:31])[CH:30]=1)=O)C.[O-]S([O-])(=O)=O.[Mg+2]>O1CCOCC1.ClCCl.CO.O>[C:5]1([C:11]2[N:12]=[C:13]3[N:18]=[C:17]([NH:19][C:24]([C:26]4[C:27]([NH:32][C:33]5[CH:38]=[N:37][CH:36]=[N:35][CH:34]=5)=[N:28][N:29]([CH3:31])[CH:30]=4)=[O:23])[CH:16]=[CH:15][N:14]3[CH:20]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 16682925TrimethylaluminumHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amineHCID 67389410HCID 67389410, compound

Product 1

HCID 67387982HCID 67387982, compoundYield 28%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Trimethylaluminum (2M solution in toluene, 0.3 ml) was added to a stirred suspension of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 128 mg) in dioxane (5 ml), and the mixture was stirred for 2 h at RT. 1-Methyl-3-(pyrimidin-5-ylamino)-1H-pyrazole-4-carboxylic acid ethyl ester (50 mg) was then added in one portion, and the mixture was heated to 100° C. for 17 h. Upon cooling, water (0.5 ml) was added, followed by small amounts of methanol and dichloromethane to get an almost clear solution. Some MgSO4 was added, the mixture was stirred for 15 min, and filtered. The filtrate was concentrated, and the title compound (23 mg, 28%) was isolated from the residue by column chromatography (silica gel, dichloromethane/methanol gradient), followed by trituration (methanol).

Workup

  1. temperaturethe mixture was heated to 100° C. for 17 h
  2. temperatureUpon cooling
  3. customto get an almost clear solution
  4. stirringthe mixture was stirred for 15 min
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-beb1e821e44b43cc8d73a78f253b54a0
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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