Water → HCID 57990385, compound

HRID 2281543Notes

Reaction equation

HRID 2281543 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][C:11]([O:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:16])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C.O>CC#N.CCOC(C)=O>[Br:1][C:2]1[C:3]([N:22]2[CH2:23][CH2:24][CH:19]([CH2:18][NH:17][C:15](=[O:16])[O:14][C:11]([CH3:12])([CH3:10])[CH3:13])[CH2:20][CH2:21]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 57990385HCID 57990385, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-bromo-2,4-dichloropyrimidine (0.256 mL, 2.00 mmol) and 4-N-Boc-aminomethylpiperidine (428 mg, 2.00 mmol) in CH3CN (5 mL), DIEA (0.700 mL, 4.02 mmol) was added. The mixture was stirred at room temperature for 40 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 tert-butyl (1-(5-bromo-2-chloropyrimidin-4-yl)piperidin-4-yl)methylcarbamate (610 mg).

Workup

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

Sources & evidence

ORD record
ord-ae34e8aaa8194bf4963a0ae38359fc21
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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