Trimethylaluminum → HCID 66678542, compound

HRID 1619091Notes

Reaction equation

HRID 1619091 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[CH:18]=[C:17]([C:19]2[C:24](Br)=[CH:23][N:22]=[C:21]([NH2:26])[N:20]=2)[N:16]([CH3:27])[CH:15]=1)=[O:13])[CH3:2].[CH3:28][Al](C)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[CH:18]=[C:17]([C:19]2[C:24]([CH3:28])=[CH:23][N:22]=[C:21]([NH2:26])[N:20]=2)[N:16]([CH3:27])[CH:15]=1)=[O:13])[CH3:2]

Participants

5

Reactant 2

HCID 16682925TrimethylaluminumHCID 66678556HCID 66678556, compound

Product 1

HCID 66678542HCID 66678542, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-(2-Amino-5-bromo-pyrimidin-4-yl)-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (83.7 mg, 0.1954 mmol) in 4 mL of dry THF, AlMe3 (1M in toluene, 0.488 mL, 0.977 mmol) and Pd(PPh3)4 (22.6 mg, 0.0195 mmol) were added under argon. The mixture was heated at 65° C. for 1 h. After dilution with water and extraction with CH2Cl2 the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude was treated with Et2O affording 58.8 mg (83%) of the desired product.

Workup

  1. extractionAfter dilution with water and extraction with CH2Cl2 the organic layer
  2. dry with materialwas dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude was treated with Et2O affording 58.8 mg (83%) of the desired product

Sources & evidence

ORD record
ord-8bd6f344b1794213872a45d177b7c620
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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