Ethyl Acetate → HCID 86714773, compound

HRID 1055119Notes

Reaction equation

HRID 1055119 reaction equation
[C:1]([NH:5][NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]([O:18][CH2:19][CH2:20]Br)(=[O:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(#N)C.[Cl-].[Na+].O>[C:1]([N:5]([CH2:16][C:15]([O:18][CH2:19][CH3:20])=[O:17])[NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 86714772HCID 86714772, compound2×

Product 1

HCID 86714773HCID 86714773, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 4-(2-tert-butylhydrazinyl)-2-chloro-5-fluoropyrimidine, 151a, (1.50 g, 6.86 mmol) in acetonitrile (68 mL) was added 2-bromoethyl acetate (0.84 mL, 7.55 mmol) and K2CO3 (2.28 g, 16.46 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted into EtOAc and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (30% EtOAc/Hexanes) to afford 1 g of the desired product: 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=3.1 Hz, 1H), 4.16 (dt, J=7.1, 5.9 Hz, 2H), 3.74 (s, 2H), 1.30-1.23 (m, 3H), 1.20 (s, 9H). LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.69 minutes (M+H) 305.09.

Workup

  1. dry with materialThe organic phase was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-fe097c525eaa46c7972a91b068a362d1
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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