Diisopropylethylamine → HCID 178526810, compound

HRID 1363203Notes

Reaction equation

HRID 1363203 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 178511715HCID 178511715, compound

Product 1

HCID 178526810HCID 178526810, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4-dicloro-5-nitropyrimidine (930 mg) in DCM (40 mL) was treated with DIEA (0.9 mL) and trans-4-aminocyclohexanol (345 mg) at −78° C. for 6 hours. The mixture was allowed to slowly warm to room temperature and stirred for 12 more hours. The solvent was evaporated and the crude mixture was purified by silica gel chromatography (DCM:EtOAc 70:30) to provide 630 mg of the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe crude mixture was purified by silica gel chromatography (DCM:EtOAc 70:30)

Sources & evidence

ORD record
ord-bc4345afa01246d882170fdd1dec81be
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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