Triethylamine → (E)-N-[2-[(5-Ethyl-6-methyl-pyrimidin-4-yl)amino]ethyl]-4-methyl-pent-2-enamide

HRID 333058Notes

Reaction equation

HRID 333058 reaction equation
[CH3:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[CH2:41]([C:43]1[C:44]([NH:50][CH2:51][CH2:52][NH2:53])=[N:45][CH:46]=[N:47][C:48]=1[CH3:49])[CH3:42]>CN(C=O)C.C(#N)C.C(OCC)(=O)C>[CH2:41]([C:43]1[C:44]([NH:50][CH2:51][CH2:52][NH:53][C:5](=[O:7])/[CH:4]=[CH:3]/[CH:2]([CH3:1])[CH3:8])=[N:45][CH:46]=[N:47][C:48]=1[CH3:49])[CH3:42]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 6420393-Isopropyl acrylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66834918N-(5-Ethyl-6-methyl-pyrimidin-4-yl)ethane-1,2-diamine hydrochloride

Product 1

HCID 56947331(E)-N-[2-[(5-Ethyl-6-methyl-pyrimidin-4-yl)amino]ethyl]-4-methyl-pent-2-enamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-4-Methylpent-2-enoic acid (46 mg, 0.4 mmol), HBTU (152 mg, 0.4 mmol) and triethylamine (82 μl, 0.6 mmol) were dissolved in a 1:1 mixture of anhydrous DMF and anhydrous acetonitrile (2 ml), after 20 minutes N-(5-ethyl-6-methyl-pyrimidin-4-yl)ethane-1,2-diamine hydrochloride (40 mg, 0.185 mmol) was added. The mixture was stirred at room temperature for 2 hours and left to stand at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 9 mg (0.033 mmol, 18%).

Workup

  1. additionwas added
  2. waitleft
  3. waitto stand at room temperature overnight
  4. washwashed with water, saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  8. customto yield 9 mg (0.033 mmol, 18%)

Sources & evidence

ORD record
ord-8df575209538467492bad8d2ae26095d
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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