Triethylamine → HCID 178452418, compound

HRID 2194588Notes

Reaction equation

HRID 2194588 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH:10]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.Cl.[CH3:22][C@@H:23]1[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]1.CCN(CC)CC>CCO>[Br:1][C:2]1[C:3]([O:9][CH:10]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=[N:4][C:5]([NH:29][C@H:26]2[CH2:27][CH2:28][C@@H:23]([CH3:22])[CH2:24][CH2:25]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86761723Tert-butyl 3-(5-bromo-2-chloropyrimidin-4-yloxy)azetidine-1-carboxylateHCID 178461306HCID 178461306, compound

Product 1

HCID 178452418HCID 178452418, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3-(5-bromo-2-chloropyrimidin-4-yloxy)azetidine-1-carboxylate (6 g, 16.4 mmol), cis-4-methylcyclohexanamine hydrochloride (2.4 5g, 16.4 mmol) and Et3N (7 mL, 49.2 mmol) in EtOH (20 mL) was executed in microwave reactor at 130° C. for 2 h. The resulting mixture was concentrated under vacuum. The residue was purified by flash chromatography (silica gel, eluted by 10 to 20% ethyl acetate in DCM) to give the titled compound (6.5 g, 90% yield). MS (ESI) m/z: Calc. 440.1 (M+). Found: 442.1 (M++2).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customThe residue was purified by flash chromatography (silica gel, eluted by 10 to 20% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-ee59c58ea6254499a0476bfd7c8e61bb
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

Loading…