2-Bromopyrimidine → HCID 178420119, compound

HRID 230391

Reaction equation

HRID 230391 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=2)[NH2:12])=[CH:2]1.Br[C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1>C(O)CCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH:12][C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[C:13]2[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 783452-BromopyrimidineHCID 178511782HCID 178511782, compound

Product 1

HCID 178420119HCID 178420119, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

(1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)ethanamine (2 g; 0.0066 mol; prepared according to experimental conditions analogous to the preceding examples and using the appropriate starting compounds and reaction products) was diluted in 10 ml n-butanol. 2-bromopyrimidine (1 g; 0.0066 mol) and then diisoethylamine (1.15 ml; 0.0066 mol) were added dropwise. The mixture was then heated to around 80° C. for about 16 hours. The n-butanol was evaporated and the residue taken up in water and ethyl acetate. The organic phase was washed with water and then with a saturated solution of sodium chloride before being dried over magnesium sulfate and concentrated using a rotative evaporator. After purification over a silica column (eluent: ethyl acetate-heptane/7-3, followed by CH2Cl2-MeOH-NH4OH/95-4.5-0.5 and ethyl acetate). A white powder was obtained (yield of 20%). Free base. Melting point: 138-140° C. MH+=381.2.

Workup

  1. customprepared
  2. customcompounds and reaction products)
  3. additionwere added dropwise
  4. customThe n-butanol was evaporated
  5. washThe organic phase was washed with water
  6. dry with materialwith a saturated solution of sodium chloride before being dried over magnesium sulfate
  7. concentrationconcentrated
  8. customa rotative evaporator
  9. customAfter purification over a silica column (eluent: ethyl acetate-heptane/7-3, followed by CH2Cl2-MeOH-NH4OH/95-4.5-0.5 and ethyl acetate)
  10. customA white powder was obtained (yield of 20%)

Sources & evidence

ORD record
ord-f0b40a11566f4d5eb5fcbf1094f056f3
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Linked notes

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