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3-Oxotetrahydrofuran → HCID 89923682, compound

HRID 626984
Notes
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Reaction equation

HRID 626984 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.C([Li])CCC.[O:14]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]1>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:16]2([OH:19])[CH2:17][CH2:18][O:14][CH2:15]2)=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5293923-OxotetrahydrofuranHCID 70066515-Bromo-2-iodopyrimidineHCID 178418339Butyllithium

Product 1

HCID 89923682HCID 89923682, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140Toluene
Solvent

Conditions

Temperature
-78 °C

Procedure

5-Bromo-2-iodopyrimidine (10 g, 35.1 mmol) was dissolved in dry toluene (100 mL) and cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 14.7 mL) was added dropwise and the reaction mixture was aged for 30 minutes prior to dropwise addition of oxolan-3-one (2.97 mL, 38.6 mmol). The reaction mixture was stirred at −78° C. for 30 minutes, then allowed to warm to room temperature for 1 h. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed successively with water and brine, then dried over magnesium sulphate. The solvent was removed under reduced pressure to afford a dark yellow oil. The crude material was purified by chromatography on silica (Biotage, 100 g cartridge), eluting with 0-100% ethyl acetate in heptanes, to afford the title compound (2.15 g, 25% at 86% purity) as a yellow oil. δH (500 MHz, DMSO-d6) 9.01 (s, 2H), 5.66 (s, 1H), 3.99-3.93 (m, 2H), 3.88-3.77 (m, 2H), 2.46 (dt, J 12.6, 8.9 Hz, 1H), 2.16 (ddd, J 12.6, 6.4, 3.5 Hz, 1H).

Workup

  1. temperatureto warm to room temperature for 1 h
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed under reduced pressure
  6. customto afford a dark yellow oil
  7. customThe crude material was purified by chromatography on silica (Biotage, 100 g cartridge)
  8. washeluting with 0-100% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-7d4e0315e0ab45b2837799ef39f27430
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309243B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes