HCID 89601756, compound → HCID 89602037, compound

HRID 570913Notes

Reaction equation

HRID 570913 reaction equation
[C:1]([N:4](C(OC(C)(C)C)=O)[N:5]1[CH2:10][C:9]([CH:11]=[O:12])=[N:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2].[CH3:28][Mg+].[Br-]>C1COCC1>[C:1]([NH:4][N:5]1[CH2:10][C:9]([CH:11]([OH:12])[CH3:28])=[N:8][N:7]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 89601756HCID 89601756, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 89602037HCID 89602037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[acetyl(tert-butoxycarbonyl)amino]-6-formyl-3-oxo-5H-1,2,4-triazine-2-carboxylate (1.15 g, 3.00 mmol) [prepared according to Example 1, Step F] in THF (11.0 mL) at 0° C. was slowly added MeMgBr (3M solution in Et2O, 1.50 mL, 4.50 mmol) via syringe. The reaction mixture was allowed to warm to room temperature and stirred for another 20 h. The reaction mixture was quenched with sat NH4Cl solution and the aqueous layer extracted EtOAc. After washing of the combined organic layers with brine and drying (Na2SO4), the solvent was removed in vacuo to give the desired product as a viscous oil. LCMS (Method I) RT 1.19 min. [M+Na]+ 323.

Workup

  1. customat 0° C.
  2. customThe reaction mixture was quenched with sat NH4Cl solution
  3. extractionthe aqueous layer extracted EtOAc
  4. washAfter washing of the combined organic layers with brine
  5. dry with materialdrying (Na2SO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-55ec291e216b48debb08faea94e36022
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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