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Hydrochloric Acid → trans-3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexanol

HRID 2189057
Notes
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Reaction equation

HRID 2189057 reaction equation
CO[CH2:3][CH2:4][O:5]C.[OH-:7].[Na+].[Br:9][C:10]1[C:18]2[C:17](Cl)=[N:16][CH:15]=[N:14][C:13]=2[O:12][C:11]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:9][C:10]1[C:18]2[C:17]([O:5][C@H:4]3[CH2:3][CH2:20][CH2:11][C@H:10]([OH:7])[CH2:18]3)=[N:16][CH:15]=[N:14][C:13]=2[O:12][C:11]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 580168535-Bromo-4-chloro-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 86653757trans-3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexanol

Reagents, catalysts & solvents 3

HCID 94433
Tetrabutylammonium hydrogen sulfate
Catalyst
HCID 962WaterSolvent2×
HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 1.1 g (8.88 mmol) of cis/trans-cyclohexanediol at 70° C. in 10 ml of toluene and 5 ml of 1,2-dimethoxyethane and add 2.84 g of 50% sodium hydroxide solution (35.5 mmol). Add water until a biphasic reaction mixture forms. Add 120.6 mg (3.55 mmol) of tetra-n-butylammonium hydrogen sulphate and 1.10 g (3.55 mmol) of 5-bromo-4-chloro-6-phenylfuro[2,3-d]pyrimidine, and stir the mixture vigorously at 70° C. for 1 h. After cooling, add the reaction mixture to water and neutralize with conc. hydrochloric acid. Extract the aqueous phase three times with ethyl acetate. Combine the organic phases, wash with satd. sodium hydrogen sulphate solution, dry over magnesium sulphate and concentrate under reduced pressure. Purify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→3:1). 0.63 g of the title compound is obtained (45.6% of theory).

Workup

  1. temperatureAfter cooling
  2. extractionExtract the aqueous phase three times with ethyl acetate
  3. washwash with satd
  4. dry with materialsodium hydrogen sulphate solution, dry over magnesium sulphate
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→3:1)

Sources & evidence

ORD record
ord-237552ed339e4e608b4411e6b098bc7c
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324222B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes