Water → Ethyl 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylate

HRID 533467

Reaction equation

HRID 533467 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.[C:14]([N:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(C(C)C)C(C)C.O>CC#N.CCOC(C)=O>[C:17]([O:16][C:14]([N:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH:27][C:6]2[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:22]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 58098693Ethyl 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylateYield 94.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (332 mg, 1.50 mmol), 1Boc-3-aminomethylpyrrolidine (300 mg, 1.50 mmol) and DIEA (0.650 mL, 3.73 mmol) in CH3CN (6 mL) was stirred at room temperature for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give ethyl 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylate (544 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialwith 5% NaHCO3, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2172314c82db455889bd282d7537bf2a
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Linked notes

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