Triethylamine → HCID 68181617, compound

HRID 1398677Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:9]3[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:8]=3[N:7]=2)[CH2:2]1.C(N(CC)CC)C.Br[CH2:31][CH2:32][OH:33]>>[NH2:17][C:13]1[N:12]=[C:11]([N:10]2[C:9]3[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:8]=3[N:7]=[C:6]2[O:5][CH:3]2[CH2:2][N:1]([CH2:31][CH2:32][OH:33])[CH2:4]2)[CH:16]=[CH:15][N:14]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 108982-Bromoethanol

HCID 68181840HCID 68181840, compound

Product 1

HCID 68181617HCID 68181617, compoundYield 50%

Procedure

A mixture of 4-[2-(azetidin-3-yloxy)-6-bromo-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (2 g, 0.44 mmol, 8% purity) and triethylamine (1.5 mL) in 2-bromoethan-1-ol (1.5 mL) was stirred at room temperature for 12 h. The reaction mixture was purified on a C18 column (water/acetonitrile, 5:95-80:20) to yield 100 mg (50%) of 2-(3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidin-1-yl)ethan-1-ol as a yellow solid: LC-MS: m/z=+405 (M+H)+.

Workup

customThe reaction mixture was purified on a C18 column (water/acetonitrile, 5:95-80:20)

Sources & evidence

ORD record: ord-14854e9b517e47378342d3fabe34982f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

Loading…