2,6-Diethylaniline → HCID 60152323, compound

HRID 1406016Notes

Reaction equation

HRID 1406016 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].[Li]N([Si](C)(C)C)[Si](C)(C)C.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]2[N:35]=[C:34]3[C:36]4[N:43]([CH3:44])[N:42]=[C:41]([C:45](OCC)=[O:46])[C:37]=4[CH2:38][CH2:39][CH2:40][C:33]3=[CH:32][N:31]=2)=[C:25]([O:50][CH3:51])[CH:24]=1>C1COCC1>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]2[N:35]=[C:34]3[C:36]4[N:43]([CH3:44])[N:42]=[C:41]([C:45]([NH:5][C:4]5[C:6]([CH2:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:3]=5[CH2:1][CH3:2])=[O:46])[C:37]=4[CH2:38][CH2:39][CH2:40][C:33]3=[CH:32][N:31]=2)=[C:25]([O:50][CH3:51])[CH:24]=1

Participants

5

Reactant 3

HCID 113692,6-DiethylanilineHCID 68295422HCID 68295422, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 60152323HCID 60152323, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-diethylaniline (0.300 g, 2.01 mmol) in 10 mL of anhydrous THF under argon, 1M in THF solution of LiN(TMS)2 (4.02 mL, 4.02 mmol) at 0° C. were added dropwise. The mixture was stirred at 0° C. for 10 minutes then ethyl 9-[(4-bromo-2-methoxyphenyl)amino]-1-methyl-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxylate (0.300 g, 0.67 mmol) in 10 mL of anhydrous THF at 0° C. were added dropwise. Ice bath was removed and the mixture was stirred at room temperature for 1 hour. Water (20 mL) was added and the mixture was extracted with AcOEt (2×30 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent evaporated to dryness. The crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/cyclohexane 1/1) to afford 0.350 g (95% yield) of the title compound as a white solid.

Workup

  1. customIce bath was removed
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. additionWater (20 mL) was added
  4. extractionthe mixture was extracted with AcOEt (2×30 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customthe solvent evaporated to dryness
  7. customThe crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/cyclohexane 1/1)

Sources & evidence

ORD record
ord-e21ef177d077401580fd203d6461c4c7
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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