Triethylamine → HCID 86707763, compound

HRID 2410109Notes

Reaction equation

HRID 2410109 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.Cl.[CH3:12][C:13]1([OH:17])[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][C:13]([CH3:12])([OH:17])[CH2:14]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 36631435-Bromo-2-chloro-4-methoxypyrimidineHCID 115427813-methylazetidin-3-ol Hydrochloride2×

Product 1

HCID 86707763HCID 86707763, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-2-chloro-4-methoxypyrimidine (3.5 g, 15.7 mmol), 3-methylazetidin-3-ol hydrochloride (2.90 g, 23.5 mmol), and Et3N (4.4 mL, 31.3 mmol) in THF (50 mL) was stirred for 18 h at rt. 3-Methylazetidin-3-ol hydrochloride (1 g) was added. The reaction mixture was stirred for 72 h at rt and concentrated. The residue was purified by flash chromatography (hexane/EtOAc 1:1) to afford 2.5 g of the title compound. tR: 0.81 min (LC-MS 2); ESI-MS: 274.2 [M+H]+ (LC-MS 2); Rf: 0.25 (hexane/EtOAc 1:1).

Workup

  1. stirringThe reaction mixture was stirred for 72 h at rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-a8f40cfb431644949604ec94b6d59de3
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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