Cesium carbonate → HCID 22260370, compound

HRID 227231Notes

Reaction equation

HRID 227231 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:25][CH3:26].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:33][CH:34](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:35]>CN(C=O)C>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][N:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:35][CH2:34][Cl:33])=[C:3]([O:25][CH3:26])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21956426HCID 21956426, compoundHCID 135545160HCID 135545160, compound

Product 1

HCID 22260370HCID 22260370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the DMF solution (10 mL) of tert-butyl 4-(7-hydroxy-6-methoxyquinazolin-4-yl)piperazinecarboxylate (1.8 g, 5 mmol), Cs2CO3 (3.3 g, 10 mmol) added 1-chloroethyl-tosylate (1.8 mL, 10 mmol). The mixture was stirred overnight at room temperature. The solvent was evaporated and the crude residue was purified by RP-HPLC (reverse-phase high performance liquid chromatography) to afford the intermediate tert-butyl-4-[6-methoxy-7-(2-chloroethoxy)quinazolin-4-yl]piperazinecarboxylate as the desired product (850 mg, 40%). MS(ES) 423 (M+H)

Workup

  1. customThe solvent was evaporated
  2. customthe crude residue was purified by RP-HPLC (reverse-phase high performance liquid chromatography)

Sources & evidence

ORD record
ord-f86989d98c50481498ccac55ea184448
Source dataset
uspto-grants-2009_07
Patent number
US07560461B2

Reaction notes

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