Water → HCID 58014785, compound

HRID 1096506Notes

Reaction equation

HRID 1096506 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.Cl.[C:15]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH2:29])[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(N(CC)CC)C.O>CC#N.CCOC(C)=O>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][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)[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 2756034tert-Butyl 4-(aminomethyl)piperidine-1-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 58014785HCID 58014785, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.221 g, 1.00 mmol), 1-Boc-4-aminomethylpiperidine hydrochloride (0.251 g, 1.00 mmol) and triethylamine (0.556 mL, 4.00 mmol) in CH3CN (10 mL) was stirred at room temperature for 20 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)piperidin-4-yl)methylamino)-2-chloropyrimidine-5-carboxylate (0.390 g).

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-e6e28d44ad72479daca8e1b14e41e0e8
Source dataset
uspto-grants-2012_03
Patent number
US08138339B2

Reaction notes

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