HCID 58458933, compound → HCID 58458917, compound

HRID 390331Notes

Reaction equation

HRID 390331 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[C:8]2[N:13]([C:14](=[O:18])[C:15]=1[O:16][CH3:17])[CH2:12][CH2:11][O:10][C:9]2([CH3:20])[CH3:19])=[O:5].[CH3:22][Mg+].[Br-]>C1COCC1.CCOCC>[C:4]([C:6]1[N:7]=[C:8]2[N:13]([C:14](=[O:18])[C:15]=1[O:16][CH3:17])[CH2:12][CH2:11][O:10][C:9]2([CH3:19])[CH3:20])(=[O:5])[CH3:22]

Participants

5

Reactant 2

HCID 58458933HCID 58458933, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 58458917HCID 58458917, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,3-dimethoxy-N,9,9-trimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide (0.40 g, 1.35 mmol, 1.0 equiv) in THF (13 mL) at 0° C. (ice/water bath) under a nitrogen atmosphere, was added CH3MgBr (0.63 mL of a 3 M solution in ether, 1.88 mmol, 1.4 equiv). After stirring 3 h, the reaction was cautiously quenched by addition of 1N HCl (10 mL). After stirring 1 h, the reaction was poured into water and extracted with CH2Cl2 (×5). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was purified by silica gel chromatography (20-100% ethyl acetate/hexane) to provide the title compound (0.054 g, 16% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.98 (s, 3H), 3.96-4.05 (m, 4H), 2.52 (s, 3H), 1.61 (s, 6H); LCMS (ES+, (M+H)+) m/z 253.23.

Workup

  1. customthe reaction was cautiously quenched by addition of 1N HCl (10 mL)
  2. stirringAfter stirring 1 h
  3. additionthe reaction was poured into water
  4. extractionextracted with CH2Cl2 (×5)
  5. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography (20-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-73944ceb6ca0438895edf1f5ff8a8a31
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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