Water → HCID 21075874, compound

HRID 1374151Notes

Reaction equation

HRID 1374151 reaction equation
C1C=C[C:4]2N(O)N=N[C:5]=2[CH:6]=1.[OH2:11].N1C=C([C:18]([OH:20])=[O:19])C=NC=1.C[CH2:22][N:23]=[C:24]=[N:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])C.C(N([CH2:37][CH3:38])CC)C>CN(C=O)C>[N:23]1[CH:22]=[C:27]([C:28]([NH:29][C:31]2([C:18]([O:20][CH2:37][CH3:38])=[O:19])[CH2:4][CH2:5][CH2:6]2)=[O:11])[CH:26]=[N:25][CH:24]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78346Pyrimidine-5-carboxylic acid

Product 1

HCID 21075874HCID 21075874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature, stirred solution of the above mentioned amine hydrochloride (1.03 g, 5.73 mmol) in DMF (30.0 mL) was added HOBt.H2O (0.879 g, 5.73 mmol), pyrimidine-5-carboxylic acid (0.783 g, 6.31 mmol), EDCI (1.21 g, 6.31 mmol) and lastly triethylamine (1.60 mL, 11.5 mmol). After overnight stirring (ca. 15 h) most of the solvent was removed under reduced pressure. The residue was then diluted with EtOAc and 5% aqueous sodium bicarbonate. This aqueous layer was extracted twice with EtOAc. The combined organics were washed with saturated copper (II) sulfate, half brine (twice) and then brine. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to obtain a residue, which was subject to silica gel chromatography. Collection of the product containing fractions and removal of solvent yielded ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclobutanecarboxylate (0.939 g) as a white crystalline solid, giving proton NMR and LC/MS data consistent with theory.

Workup

  1. stirringAfter overnight stirring (ca. 15 h) most of the solvent
  2. customwas removed under reduced pressure
  3. additionThe residue was then diluted with EtOAc and 5% aqueous sodium bicarbonate
  4. extractionThis aqueous layer was extracted twice with EtOAc
  5. washThe combined organics were washed with saturated copper (II) sulfate, half brine (twice) and then brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto obtain a residue, which
  10. customCollection of the product
  11. additioncontaining
  12. customfractions and removal of solvent

Sources & evidence

ORD record
ord-12960127970444d89872c39d11410080
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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