Triethylamine → HCID 86707764, compound

HRID 2410110Notes

Reaction equation

HRID 2410110 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.Cl.[OH:12][CH:13]1[CH2:16][NH:15][CH2:14]1.CCN(CC)CC>C1COCC1>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([N:15]2[CH2:16][CH:13]([OH:12])[CH2:14]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27592903-Hydroxyazetidine hydrochloride2×HCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 86707764HCID 86707764, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-2-chloro-4-methoxypyrimidine (3.3 g, 14.8 mmol), 3-hydroxyazetidine hydrochloride (3.2 g, 29.5 mmol), and Et3N (4.3 mL, 31.0 mmol) in THF (50 mL) was stirred for 18 h at rt. 3-Hydroxyazetidine hydrochloride (1 g) was added. The reaction mixture was stirred for 24 h at rt and concentrated. The residue was diluted in CH2Cl2/water and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (hexane/EtOAc, 1:1) to afford 3 g of the title compound. tR: 0.73 min (LC-MS 2); ESI-MS: 260.1/262.1 [M+H]+ (LC-MS 2); Rf=0.18 (hexane/EtOAc 1:1).

Workup

  1. stirringThe reaction mixture was stirred for 24 h at rt
  2. concentrationconcentrated
  3. additionThe residue was diluted in CH2Cl2/water
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-0bcf8049760e469d97b134139cc4766d
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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