Dimethyl Sulfoxide → HCID 89442751, compound

HRID 2284055Notes

Reaction equation

HRID 2284055 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.Cl.N1(C[CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:23]=N[CH:25]=[C:26]([C:28]([F:31])(F)F)[CH:27]=3)[N:19]=[C:18]2[CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)CCC1.[C:38]([O-:41])([O-])=O.[Cs+].[Cs+].O.[CH3:45]S(C)=O>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([N:35]2[CH2:34][CH2:33][CH:32]([C:18]3[N:17]([CH2:16][CH2:38][OH:41])[CH:21]=[C:20]([C:22]4[CH:23]=[CH:45][C:28]([F:31])=[C:26]([CH3:25])[CH:27]=4)[N:19]=3)[CH2:37][CH2:36]2)[C:2]=1[Br:1]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 10796Cesium carbonateHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 89442682HCID 89442682, compound

Product 1

HCID 89442751HCID 89442751, compound

Conditions

Temperature
100 °C

Procedure

A reaction mixture of 5-bromo-6-chloro-pyrimidin-4-ylamine (370.00 mg; 1.78 mmol; 1.00 eq.), 2-[4-(4-fluoro-3-methyl-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethanol hydrochloride (3) (732.67 mg; 1.78 mmol; 1.00 eq.), and Cs2CO3 (2313.40 mg; 7.10 mmol; 4.00 eq.) in DMSO 10 ml, stirred at 100° C. for overnight, cooled, poured into water 60 ml, stirred for 15 mins, filtered, collected light yellow solid, which was washed with water, dried, got title compound, 750 mg, 88.9%.

Workup

  1. temperaturecooled
  2. stirringstirred for 15 mins
  3. filtrationfiltered
  4. customcollected light yellow solid, which
  5. washwas washed with water
  6. customdried

Sources & evidence

ORD record
ord-a759b5f63f92443083e206f9bf1203e7
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

Loading…