Triethylamine → HCID 22235943, compound

HRID 1744053Notes

Reaction equation

HRID 1744053 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:6][CH:7]=1.C1CN([P+](O[N:34]2N=[N:41][C:36]3C=CC=C[C:35]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14]([NH:41][CH2:36][C:35]#[N:34])=[O:16])=[N:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69152255HCID 69152255, compound

Product 1

HCID 22235943HCID 22235943, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the crude N-(5-bromo-2-pyrimidinyl)leucine (1.3 g, 4.2 mmol), PyBOP (2.62 g, 5.04 mmol), aminoacetonitrile hydrochloride (930 mg, 10.08 mmol) in dry DMF (50 mL) under dry nitrogen was added triethylamine (2.4 mL, 16.8 mmol) dropwise and the reaction was stirred overnight. Aqueous Sat. NaHCO3 was added and the product extracted with Et2O (2×), dried on Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 1/1) to afford 2-[(5-bromo-2-pyrimidinyl)amino]-N-(cyanomethyl)-4-methylpentanamide.

Workup

  1. extractionthe product extracted with Et2O (2×)
  2. customdried on Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 1/1)

Sources & evidence

ORD record
ord-c2d47383957547539fd868052854d09a
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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