Potassium Carbonate → HCID 46892945, compound

HRID 2065519Notes

Reaction equation

HRID 2065519 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[N:5]2[CH:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=[C:4]2[CH:3]=1.[CH2:21]([N:23]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)[S:24]([CH3:27])(=[O:26])=[O:25])[CH3:22].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH2:21]([N:23]([C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=3)[N:5]3[CH:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=[C:4]3[CH:3]=2)[CH:33]=1)[S:24]([CH3:27])(=[O:25])=[O:26])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68490306HCID 68490306, compoundHCID 86604556HCID 86604556, compound

Product 1

HCID 46892945HCID 46892945, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-chloro-2-isopropyl-N-(5-methyl-1H-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine (0.17 mmol, 0.05 g), 3-(N-ethylmethylsulfonamido)phenylboronic acid (0.35 mmol) and (Ph3)4Pd (O) (0.086 mmol, 0.1 g) were stirred in dioxane (3 mL) and sat. K2CO3 (1.5 mL) The reaction mixture was heated to 150° C. using a microwave reactor for 20 minutes. The mixture was then concentrated and purified by LC-MS to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (t, J=7.07 Hz, 3H) 1.35 (d, J=6.82 Hz, 6H) 2.29 (s, 3H) 3.04 (s, 3H) 3.76 (q, J=7.07 Hz, 2H) 6.70 (s, 1H) 7.57 (s, 1H) 7.59-7.67 (m, 2H) 8.11 (d, J=7.58 Hz, 1H) 8.17 (s, 1H) 8.45 (s, 1H) 10.80 (s, 1H) 12.35 (s, 1H); ESI-MS: m/z calc'd for C22H27N7O2S 453.56; found 454.4 (M+H)+

Workup

  1. customfor 20 minutes
  2. concentrationThe mixture was then concentrated
  3. custompurified by LC-MS

Sources & evidence

ORD record
ord-6dd8947af5e347528d042e4f42f7aba9
Source dataset
uspto-grants-2012_10
Patent number
US08288536B2

Reaction notes

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