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Sodium Iodide → (R)-Acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propyl ester

HRID 219706
Notes
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Reaction equation

HRID 219706 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[I-].[Na+].[C:30]([O:33][CH2:34][C@H:35]([CH3:38])[CH2:36]Br)(=[O:32])[CH3:31]>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:36][C@@H:35]([CH3:38])[CH2:34][O:33][C:30](=[O:32])[CH3:31])[CH2:17][CH2:16]2)[CH:8]=[C:9]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 10465240(S)-(+)-1-Acetoxy-3-bromo-2-methyl-propaneHCID 666733902-tert-Butyl-4-cyclobutyl-6-(piperazin-1-yl)pyrimidine

Product 1

HCID 131729778(R)-Acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propyl esterYield 106.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.87 g of 2-tert-butyl-4-cyclobutyl-6-piperazin-1-yl-pyrimidine (14.1 mmol) were stirred in 30 ml of dimethylformamide at room temperature. 3.18 g of triethylamine (63.1 mmol), 0.235 g of sodium iodide (1.57 mmol), 3.01 g of (S)-(+)-1-acetoxy-3-bromo-2-methyl-propane (15.7 mmol) were added. The reaction mixture was stirred for 16 h at room temperature. Stirring was continued for 2 h at 95-105° C. The dimethylformamide was removed by evaporation under reduce pressure. The residue was partitioned between 100 ml of dichloromethane and 100 ml of water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give the crude product as a brownish oil (5.81 g).

Workup

  1. stirringStirring
  2. waitwas continued for 2 h at 95-105° C
  3. customThe dimethylformamide was removed by evaporation
  4. customThe residue was partitioned between 100 ml of dichloromethane and 100 ml of water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3ce4c45f426c454aa6faab8aee130180
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202868B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes