Glycerol → HCID 68181607, compound

HRID 1398667Notes

Reaction equation

HRID 1398667 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8](C(Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([OH:33])[CH:29]([OH:32])[CH2:30][OH:31]>CN(C)C=O>[NH2:20][C:16]1[N:15]=[C:14]([N:7]2[C:6]3[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:33][CH2:28][CH:29]([OH:32])[CH2:30][OH:31])[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 753GlycerolHCID 10796Cesium carbonateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 68181607HCID 68181607, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol), cesium carbonate (3.2 g, 9.82 mmol) and propane-1,2,3-triol (565 mg, 6.14 mmol) in N,N-dimethylformamide (3 mL) was stirred for 12 h at room temperature. The reaction mixture was filtered through a frit filter to remove any solid material and the filtrate was purified by Flash-Preparative HPLC to give 90 mg (19%) of 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]propane-1,2-diol as a yellow solid. 1H NMR (400 MHz, DMSO) delta 8.46 (s, 1H), 8.37 (d, J=5.2 Hz, 1H), 7.44-7.38 (m, 2H), 7.13-7.09 (m, 3H), 5.18 (d, J=5.2 Hz, 1H), 4.80 (d, J=6.0 Hz, 1H), 4.68-4.64 (m, 1H), 4.52-4.48 (m, 1H), 3.93 (d, J=4.8 Hz, 1H), 3.52-3.46 (m, 2H); LC-MS: m/z=+380 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a frit
  2. filtrationfilter
  3. customto remove any solid material
  4. customthe filtrate was purified by Flash-Preparative HPLC

Sources & evidence

ORD record
ord-4320fc0d4ffd4549b01570ac9d32e346
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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