Diisopropylethylamine → HCID 86610157, compound

HRID 1363151Notes

Reaction equation

HRID 1363151 reaction equation
[CH3:1][C@H:2]1[C@@H:7]([NH2:8])[CH2:6][CH2:5][O:4][CH2:3]1.CCN(C(C)C)C(C)C.[Cl:18][C:19]1[N:24]=[C:23](Cl)[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][N:20]=1>C1COCC1.CCOC(C)=O>[Cl:18][C:19]1[N:24]=[C:23]([NH:8][C@H:7]2[CH2:6][CH2:5][O:4][CH2:3][C@H:2]2[CH3:1])[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][N:20]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 55285641(3S,4S)-3-Methyloxan-4-amine

Product 1

HCID 86610157HCID 86610157, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.24 g of the hydrochloride salt of cis-3-methyl-tetrahydro-2H-pyran-4-amine (WO 2004/041161) and DIEA (1.5 mL) in THF (10 mL) at −78° C. was added 2,4-dichloro-5-nitropyrimidine (0.72 g). The mixture was allowed to slowly reach room temperature and stirred for 16 hours. The mixture was diluted with EtOAc and washed 3 times with brine. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. Column chromatography (20→40% EtOAc/hexanes) provided 289 mg of the title compound.

Workup

  1. customwas allowed to slowly reach room temperature
  2. washwashed 3 times with brine
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d12cdad8fa7b480b8aa600c29043501d
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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