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Ethanol → HCID 20156411, compound

HRID 986768
Notes
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Reaction equation

HRID 986768 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[N:14]=[C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]3[CH:21]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(O)C>C(Cl)Cl>[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[N:14]=[C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]3[CH:21]=2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 20156477HCID 20156477, compound

Product 1

HCID 20156411HCID 20156411, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

1.38 g (5 mmol) of 2-(1-methoxy-naphth-4-yl)-imidazo[1,2-a]pyrimidine are suspended in 50 ml of methylene chloride, cooled to -40° C. and 1.15 ml (12 mmol) of boron tribromide are added dropwise with stirring. The mixture is then stirred for 14 hours at ambient temperature, 30 ml of ethanol are added and the mixture is stirred for a further 30 minutes. It is then concentrated to dryness in vacuo and the crude product thus obtained in purified by column chromatography.

Workup

  1. stirringThe mixture is then stirred for 14 hours at ambient temperature
  2. stirringthe mixture is stirred for a further 30 minutes
  3. concentrationIt is then concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-735ed3c2659f40ed89f2b3016fd30131
Source dataset
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04716169

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes