Diisopropylethylamine → HCID 89740313, compound

HRID 2206639Notes

Reaction equation

HRID 2206639 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C@@H:7]([NH2:9])[CH3:8])[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Br:19][C:20]1[C:21](Cl)=[N:22][C:23]([Cl:26])=[N:24][CH:25]=1>C(O)C.C(OCC)(=O)C>[Br:19][C:20]1[C:21]([NH:9][C@H:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH3:8])=[N:22][C:23]([Cl:26])=[N:24][CH:25]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 67033300(1S)-1-(Oxan-4-yl)ethan-1-amine

Product 1

HCID 89740313HCID 89740313, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (S)-1-(tetrahydro-2H-pyran-4-yl)ethanamine (1.0 g, 7.75 mmol) in ethanol (15 mL) was added N,N-diisopropylethylamine (3.0 g, 23.3 mmol) and 5-bromo-2,4-dichloropyrimidine (2.0 g, 8.53 mmol) at 25° C. under N2. The reaction was stirred at 25° C. for 18 hrs. The mixture was diluted with ethyl acetate and washed with water. The crude product was purified by column chromatography on silica gel eluted with petroleum ether: ethyl acetate=20:1 to give (S)-5-bromo-2-chloro-N-(1-(tetrahydro-2H-pyran-4-yl)ethyl)Pyrimidin-4-amine (1.5 g, 60.7%) as a yellow oil.

Workup

  1. washwashed with water
  2. customThe crude product was purified by column chromatography on silica gel
  3. washeluted with petroleum ether

Sources & evidence

ORD record
ord-269ac428b7554b409915e6a074863e37
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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