Ethyl bromoacetate → HCID 178516869, compound

HRID 657166Notes

Reaction equation

HRID 657166 reaction equation
Cl.[NH2:2][C:3]1[C:8]([OH:9])=[CH:7][N:6]=[C:5](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1.[CH3:18][C:19](C)([O-:21])C.[K+].BrCC(OCC)=O>C(O)C>[C:12]1(/[CH:11]=[CH:10]/[C:5]2[NH:4][C:3]3[C:8]([O:9][CH2:18][C:19](=[O:21])[N:2]=3)=[CH:7][N:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 68484103HCID 68484103, compound

Product 1

HCID 178516869HCID 178516869, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-amino-2-[(E)-2-phenylethenyl]-5-pyrimidinol hydrochloride (250 mg, 1.0 mmol) in absolute ethanol (5 mL) was added potassium tert-butoxide (224 mg, 2.0 mmol) at room temperature. After stirring for 5 minutes, ethyl bromoacetate (0.11 mL, 1.0 mmol) was added via dropwise addition and the reaction was stirred for 18 h. The solvent was evaporated and the residue was taken up in 10% MeOH—CHCl3 and a small amount of water. The layers were separated and the aqueous phase was extracted with 10% MeOH—CHCl3 (3×). The combined organic extracts were concentrated and the resulting solid was triterated with EtOAc. The white solid was collected by filtration, yielding 106 mg (42%).

Workup

  1. stirringthe reaction was stirred for 18 h
  2. customThe solvent was evaporated
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with 10% MeOH—CHCl3 (3×)
  5. concentrationThe combined organic extracts were concentrated
  6. filtrationThe white solid was collected by filtration
  7. customyielding 106 mg (42%)

Sources & evidence

ORD record
ord-8ff8ed0bf62d41b49fc2f3108df8325e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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