Acetone → HCID 68880201, compound

HRID 1723665Notes

Reaction equation

HRID 1723665 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([S:23](=[O:34])(=[O:33])[N:24]([CH2:29][CH2:30][O:31][CH3:32])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19][CH:18]=4)[N:11]=3)=[CH:8][N:7]=[C:6]2[CH3:35])[CH2:3][CH2:2]1.C([Li])CCC.[CH3:41][C:42]([CH3:44])=[O:43].O>C1COCC1>[CH:1]1([CH2:4][N:5]2[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([S:23](=[O:33])(=[O:34])[N:24]([CH2:29][CH2:30][O:31][CH3:32])[C:25]([CH3:27])([CH3:28])[CH3:26])=[CH:21][CH:22]=4)[N:11]=3)=[CH:8][N:7]=[C:6]2[CH2:35][C:42]([OH:43])([CH3:44])[CH3:41])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 68883960HCID 68883960, compoundHCID 178418339Butyllithium

Product 1

HCID 68880201HCID 68880201, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-(1-Cyclopropylmethyl-2-methylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)-N-(t-butyl)sulphamoyl]anilino}pyrimidine (Method 78; 1.15 g, 2.31 mmol) was dissolved in anhydrous THF (80 ml), under nitrogen. The solution was cooled to −78° C. and n-butyl lithium (2.88 ml of a 1.6 N solution in hexanes, 4.62 mmol), was added slowly, maintaining the temperature at less than −65° C. The reaction mixture was then stirred at −78° C. for 30 minutes, then acetone (1187 μl, 2.54 mmol) was added and mixture allowed to warm to ambient temperature and stirred for 1 hour. The reaction mixture was then poured into water (100 ml), and extracted with EtOAc (2×50 ml). The organic extracts were combined, washed with water (50 ml), brine (50 ml), and dried. The volatiles were removed and the residue was purified by chromatography on silica gel eluting with EtOAc to give the title compound (465 mg, 36%) as a yellow solid. NMR: 0.10 (m, 2H) 0.18 (m, 2H) 0.89 (m, H) 1.07 (s, 6H) 1.12 (s, 9H) 2.75 (s, 2H) 3.15 (s, 3H) 3.38 (m, 4H) 4.54 (d, 2H) 7.11 (d, H) 7.58 (m, 3H) 7.75 (d, 2H) 8.34 (d, H) 9.8 (s, H); m/z 557.

Workup

  1. temperaturemaintaining the temperature at less than −65° C
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 1 hour
  4. extractionextracted with EtOAc (2×50 ml)
  5. washwashed with water (50 ml), brine (50 ml)
  6. customdried
  7. customThe volatiles were removed
  8. customthe residue was purified by chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-0373971ea57e42d4b5eddead16b0b30a
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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