Cesium carbonate → HCID 86620659, compound

HRID 735815Notes

Reaction equation

HRID 735815 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9](NC2N=CC(C3C=CC(OC)=CC=3)=CN=2)[CH:10]=[CH:11][C:12]=1OC)[CH3:2].COC1C=CC([NH:40][C:41]2[N:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)=[CH:43][N:42]=2)=CC=1O.[C:56]([O-])([O-])=[O:57].[Cs+].[Cs+].ClCCN(CC)CC>CN(C=O)C>[CH2:30]([N:3]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([O:57][CH3:56])[CH:10]=[CH:11][C:12]=1[N:42]1[CH:43]=[C:44]([C:47]2[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=2)[CH:45]=[N:46][CH:41]1[NH2:40])[CH2:1][CH3:2])[CH3:31]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 13364Diethylaminoethyl chlorideHCID 57632725HCID 57632725, compoundHCID 57632928HCID 57632928, compound

Product 1

HCID 86620659HCID 86620659, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

[3-(2-Diethylamino-ethoxy)-4-methoxy-phenyl]-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine can be synthesized by the following procedure. To a solution of 2-methoxy-5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenol (0.2 mmol) (from Example 5v) in anhydrous DMF (2 mL) is added Cs2CO3 (0.28 mmol) and (2-chloro-ethyl)-diethyl-amine (0.2 mmol). The reaction mixture stirred at 80° C. for 8 h and quenched with water followed by extraction with DCM (3×30 mL). The organic layer is washed with brine, dried over Na2SO4 and concentrated. Preparative LCMS purification affords the title compound (78%). MS (m/z) (M+1)+ 423.1.

Workup

  1. customquenched with water
  2. extractionfollowed by extraction with DCM (3×30 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPreparative LCMS purification

Sources & evidence

ORD record
ord-f41fa5fea1a14beaa36089c7e52eb777
Source dataset
uspto-grants-2009_09
Patent number
US07592349B2

Reaction notes

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