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Dimethylformamide → 2-Chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine

HRID 1850484
Notes
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Reaction equation

HRID 1850484 reaction equation
CN(C=O)C.[CH3:6][C:7]1([CH3:25])[CH2:11][C:10]2[C:12]([CH3:24])=[C:13]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1.[Cl:26][C:27]1[N:32]=[C:31]([Cl:33])[CH:30]=[CH:29][N:28]=1.C(N(CC)CC)C>O>[Cl:26][C:27]1[N:32]=[C:31]([N:21]2[CH2:20][CH2:19][N:18]([C:13]3[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]4[O:8][C:7]([CH3:25])([CH3:6])[CH2:11][C:10]=4[C:12]=3[CH3:24])[CH2:23][CH2:22]2)[CH:30]=[CH:29][N:28]=1.[Cl:33][C:31]1[CH:30]=[CH:29][N:28]=[C:27]([N:21]2[CH2:20][CH2:19][N:18]([C:13]3[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]4[O:8][C:7]([CH3:25])([CH3:6])[CH2:11][C:10]=4[C:12]=3[CH3:24])[CH2:23][CH2:22]2)[N:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 667597311-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

Product 2

HCID 594850032-Chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidineYield 62%
HCID 59485115
4-Chloro-2-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine
Yield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the DMF (10 mL) solution of 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (1.92 g, 7.00 mmol) synthesized in Reference example 61, 2,4-dichloropyrimidine (1.04 g, 7.00 mmol) and triethylamine (1.07 mL, 7.70 mmol) were added and the mixture was stirred at room temperature for 1 hour. To the mixture solution, water was added. The extraction was carried out by using ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5-85:15) to obtain 2-chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine 1.68 g (ethyl acetate/hexane=4:1, Rf=0.1, yield 62%) and 4-chloro-2-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine 100 mg (ethyl acetate/hexane=4:1, Rf=0.5, yield 4%).

Workup

  1. additionwere added
  2. extractionThe extraction
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5-85:15)

Sources & evidence

ORD record
ord-9442a5ed28bd4b2580e95d4722857b1b
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957069B2

Reaction notes

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