Diisopropylethylamine → HCID 68283130, compound

HRID 623996Notes

Reaction equation

HRID 623996 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[N:3][CH:2]=1.CCN(C(C)C)C(C)C.[N+:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])#[C-:20].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:9][CH:20]=[N:19][C:21]=2[C:22]([O:24][CH3:25])=[O:23])=[N:3][CH:2]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 1693064-Pyrimidinecarboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 547815Methyl isocyanoacetate

Product 1

HCID 68283130HCID 68283130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of pyrimidine-4-carboxylic acid (261 mg, 2.00 mmol) and DIPEA (0.52 mL, 2.96 mmol) in DMF (8 mL) was added methyl isocyanoacetate (0.28 mL, 2.93 mmol) at rt. The resulting yellow solution was stirred at rt for 5 min and cooled to 0° C. DPPA (0.54 mL, 2.43 mmol) was then added and the resulting solution was stirred at 0° C. for 1 h and at rt for 30 min. Aq. sat. NaHCO3-solution was added and the mixture extracted with EtOAc (4×). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification by FC (hept/EtOAc 9:1 to 100% EtOAc) yielded methyl 5-(pyrimidin-4-yl)oxazole-4-carboxylate. LC-MS conditions A: tR=0.68 min, [M+H]+=206.43.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe resulting solution was stirred at 0° C. for 1 h and at rt for 30 min
  3. extractionthe mixture extracted with EtOAc (4×)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by FC (hept/EtOAc 9:1 to 100% EtOAc)

Sources & evidence

ORD record
ord-91f954251b5e490b888da79eed680533
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

Loading…