Tetrahydrofuran → HCID 59300456, compound

HRID 603491Notes

Reaction equation

HRID 603491 reaction equation
[H-].[Na+].C1COCC1.[CH2:8]([OH:12])[CH2:9][CH2:10][OH:11].[Cl:13][C:14]1[N:19]=[C:18](Cl)[CH:17]=[CH:16][N:15]=1>[Cl-].[Na+].O>[Cl:13][C:14]1[N:19]=[C:18]([O:11][CH2:10][CH2:9][CH2:8][OH:12])[CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 59300456HCID 59300456, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a round-bottom flask charged with NaH (336 mg, 8.29 mmol, 60% dispersion in mineral oil) and THF (100 mL), 1,3-propanediol (0.91 mL, 12.6 mmol) was added dropwise [H2 evolution] at rt. The reaction mixture was stirred for 30 min, then 2,4-dichloropyrimidine (5.0 g, 33.6 mmol) was added, and the reaction mixture was stirred for an additional 72 h. Brine was slowly added and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography to provide the product (350 mg, 22%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 2.01 (qt, 2H), 2.43-2.52 (b, 1H), 3.76 (t, 2H), 4.51 (t, 2H), 6.63 (d, 1H), 8.25 (d, 1H) LC-MS: RT=1.05 min, (M+H)+ 189.1.

Workup

  1. additionwas added dropwise [H2 evolution] at rt
  2. stirringthe reaction mixture was stirred for an additional 72 h
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-b28f3436a9bc4431b830caa1c77ddee4
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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