Diisopropylethylamine → 2-chloro-5-bromo-N-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 415426Notes

Reaction equation

HRID 415426 reaction equation
[CH:1]([O:4][C:5]1[NH:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[Cl:20][C:21]1[N:26]=[C:25](Cl)[C:24]([Br:28])=[CH:23][N:22]=1>C1COCC1>[Br:28][C:24]1[C:23]([NH:10][C:7]2[CH:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[NH:9][N:8]=2)=[N:22][C:21]([Cl:20])=[N:26][CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 1784587215-Isopropoxy-1H-pyrazol-3-amine

Product 1

HCID 1784586132-chloro-5-bromo-N-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-isopropoxy-1H-pyrazol-3-amine (11.6 g, 82.1 mmol) in THF (85 ml) was added DIPEA (16 ml) and 2,4-dichloro-5-bromopyrimidine (17 g, 74.6 mmol) and the resulting solution was aged at 40° C. for 16 hours. The mixture was partitioned between EtOAc and H2O, the organic layer was washed with brine and dried. The solvents were removed under reduced pressure and column chromatography gave the title compound as a solid. m/z: 332.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washthe organic layer was washed with brine
  3. customdried
  4. customThe solvents were removed under reduced pressure and column chromatography

Sources & evidence

ORD record
ord-868a143f254e43028a58d2cee7fe666b
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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