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N-Methoxy-N-methylbenzamide → 2-Anilino4(2-benzoyl-1-isopropylimidazol-5-yl)pyrimidine

HRID 32345
Notes
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Reaction equation

HRID 32345 reaction equation
C([Li])CCC.[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:26])[CH3:25])[C:22]([CH:27]=[O:28])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CON(C)C(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:25])[CH3:26])[C:22]([C:27](=[O:28])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 113949762-Anilino4(2-benzoyl-1-isopropylimidazol-5-yl)pyrimidineYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

n-Butyllithium (3.12 ml of 1.6 M solution in hexane, 5.0 mmol) was added to a stirred solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 558 mg, 2.0 mmol) in anhydrous THF (20 ml) cooled to −70° C. The mixture was stirred for 30 minutes and then N-methoxy-N-methylbenzamide (660 mg, 4.0 mmol) was added and the reaction mixture was allowed to warm and stirred at ambient temperature for 18 hour. The reaction mixture was quenched with water (20 ml), and extracted with EtOAc (4×25 ml). The organic extracts were washed with brine (2×50 ml), dried and the volatiles removed by evaporation and the residue triturated with ether and the solid collected by filtration to give the title compound (303 mg, 43%) as a pale yellow crystalline solid. NMR (CDCl3): 1.55-1.70 (m, 8H), 5.52-5.68 (sept, 1H), 6.99 (d, 1H), 7.09 (dt, 1H), 7.18 (br s, 1H), 7.30-7.40 (m, 2H), 7.45-7.54 (m, 2H), 7.55 (s, 1H), 7.56-7.62 (m, 3H), 8.09 (d, 2H), 8.49 (d, 1 H); m/z 384.

Workup

  1. temperatureto warm
  2. stirringstirred at ambient temperature for 18 hour
  3. customThe reaction mixture was quenched with water (20 ml)
  4. extractionextracted with EtOAc (4×25 ml)
  5. washThe organic extracts were washed with brine (2×50 ml)
  6. customdried
  7. customthe volatiles removed by evaporation
  8. customthe residue triturated with ether
  9. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-484b93adf97c48f698d4757d78117903
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07427626B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes