Potassium Carbonate → HCID 57816823, compound

HRID 2197477Notes

Reaction equation

HRID 2197477 reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][NH:12]2)=[C:8]([NH2:15])[N:7]=1)[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[CH2:27][P:28]([CH3:33])(=[O:32])[O:29][CH2:30][CH3:31]>CN(C=O)C>[NH2:15][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][N:12]2[CH2:23][C:24]1[CH:25]=[C:26]([CH2:27][P:28]([CH3:33])(=[O:32])[O:29][CH2:30][CH3:31])[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57816773HCID 57816773, compoundHCID 178448875HCID 178448875, compound

Product 1

HCID 57816823HCID 57816823, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 64 (300.0 mg, 1.45 mmol) and K2CO3 (200.0 mg, 1.45 mmol) was dissolved in DMF (5 mL) and to it was added 65 (420.0 mg, 1.45 mmol). The mixture was left to stir over night at room temperature, solvent was evaporated by rotary evaporation. The remaining solid was taken up in water and the product extracted with DCM (3×50 mL). Combined organic layers were washed with water (1×50 mL) and brine (2×50 mL) and dried over Na2SO4. Product was purified by flash column eluting 0-20% methanol in ethyl acetate to give 299.4 mg (50%) 66 as a solid. 1H NMR (300 MHz, CDCl3) δ 0.818 (t, 3H), 1.15 (t, 3H), 1.24 (d, 3H), 1.27 (m, 2H), 1.43 (m, 2H), 2.99 (d, 2H), 3.28 (m, 2H), 3.87 (m, 2H), 4.01 (m, 2H), 5.09 (s, 2H), 7.11 (m, 4H), 7.36 (s, 1H). LCMS: m/z for C20H29N6O2P++H observed 417.3 at 1.76 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O.

Workup

  1. waitThe mixture was left
  2. customsolvent was evaporated by rotary evaporation
  3. extractionthe product extracted with DCM (3×50 mL)
  4. washCombined organic layers were washed with water (1×50 mL) and brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. customProduct was purified by flash column
  7. washeluting 0-20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-b0045bde014a47aa81e4f707cf434555
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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