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Potassium Carbonate → Ethyl3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoate

HRID 2234416
Notes
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Reaction equation

HRID 2234416 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH3:14])([CH3:13])[CH2:6][NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[N:28]=[C:27](Cl)[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][N:24]=1>CC(C)=O>[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH3:14])([CH3:13])[CH2:6][N:7]([C:25]1[C:26]([N+:30]([O-:32])=[O:31])=[CH:27][N:28]=[C:23]([Cl:22])[N:24]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57969950Ethyl 3-(cyclopentylamino)-2,2-dimethylpropanoate

Product 1

HCID 58153872Ethyl3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred clear colourless solution of Ethyl3-(cyclopentylamino)-2,2-dimethyl-propanoate (US 2004/0176380 A1; 29.8 g, 139.7 mmol) in the acetone (700 mL) at room temperature was added potassium carbonate (21.3 g, 153.7 mmol) followed by 2,4-dichloro-5-nitropyrimidine (Aldrich; 29.81 g, 153.7 mmol). The reaction mixture was stirred vigorously at room temperature overnight. Potassium carbonate (7.75 g, 56 mmol) was added stirring continued for a further 4 hours. The reaction mixture was concentrated in vacuo to low volume and partitioned between Ethyl Acetate (600 mL) and water (400 mL). Phases were separated and the aqueous phase re-extracted with Ethyl Acetate (1×200 ml, 1×100 ml). The combined organic extracts were dried using MgSO4 and evaporated to dryness The residue was dissolved in DCM (150 mL) and purified in two batches using a Biotage Flash 75 system with 400 g Si column, conditioned with 10% Ethyl Acetate in isohexane and eluted with 10% Ethyl Acetate in isohexane. Product containing fractions were combined and evaporated giving the title compound as a yellow oil which solidified on standing in a freezer (27.90 g 54%)

Workup

  1. stirringstirring
  2. waitcontinued for a further 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo to low volume
  4. custompartitioned between Ethyl Acetate (600 mL) and water (400 mL)
  5. customPhases were separated
  6. extractionthe aqueous phase re-extracted with Ethyl Acetate (1×200 ml, 1×100 ml)
  7. customThe combined organic extracts were dried
  8. customevaporated to dryness The residue
  9. dissolutionwas dissolved in DCM (150 mL)
  10. custompurified in two batches
  11. washeluted with 10% Ethyl Acetate in isohexane
  12. additionProduct containing fractions
  13. customevaporated

Sources & evidence

ORD record
ord-87d7ba88425148f4bca8990a092bfa68
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709471B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes