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Dimethylformamide → Ainuovirine

HRID 1643356
Notes
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Reaction equation

HRID 1643356 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:17])[CH3:16])=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH2:29][CH3:30].[CH3:31][N:32](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:29]([N:12]1[C:7]([C:5]([C:4]2[CH:3]=[C:2]([CH:20]=[C:19]([CH3:21])[CH:18]=2)[C:31]#[N:32])=[O:6])=[C:8]([CH:15]([CH3:17])[CH3:16])[C:9](=[O:14])[NH:10][C:11]1=[O:13])[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 577518946-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 25215428AinuovirineYield 48%

Reagents, catalysts & solvents 4

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To a stirred solution of 6-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione (2.14 kg, 6.09 mol) in anhydrous DMF (5 L) under nitrogen, were added zinc cyanide (428 g), DPPF (73 g), and Pd2dba3 (56 g), in this order. The mixture was heated to 110-120° C. and stirred vigorously for 2 hours. After cooling to room temperature, K2CO3 (1.88 kg) and iodoethane (1.15 L, 14.31 mol) were added to the mixture. The mixture was heated to 60-65° C. and stirred for 18 hours. After cooling to room temperature, the mixture was diluted with water (20 L). The precipitate was collected by filtration, washed with water (10 L) and then dissolved in dichloromethane (30 L). The solution was washed with water (10 L), 2N-HCl (10 L), dried with anhydrous magnesium sulfate (1 kg), and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/dichloromethane, 1:9) to afford 3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl)-5-methylbenzonitrile (951 g, 2.92 mol, 48%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe mixture was heated to 60-65° C.
  3. stirringstirred for 18 hours
  4. temperatureAfter cooling to room temperature
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water (10 L)
  7. dissolutiondissolved in dichloromethane (30 L)
  8. washThe solution was washed with water (10 L), 2N-HCl (10 L)
  9. dry with materialdried with anhydrous magnesium sulfate (1 kg)
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by silica gel column chromatography (eluent: ethyl acetate/dichloromethane, 1:9)

Sources & evidence

ORD record
ord-487be0a312ac42a9bfcf5e9d82d5198a
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08119800B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes