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1H-Indazole → 5-bromo-6-chloro-2-(1H-indazol-1-yl)pyrimidine-4-amine

HRID 63603
Notes
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Reaction equation

HRID 63603 reaction equation
[Br:1][C:2]1[C:3]([NH2:12])=[N:4][C:5](S(C)=O)=[N:6][C:7]=1[Cl:8].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[N:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[C:3]([NH2:12])=[N:4][C:5]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[N:14]2)=[N:6][C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 10796Cesium carbonateHCID 866770165-Bromo-6-chloro-2-methanesulfinylpyrimidin-4-amine2×

Product 1

HCID 903037965-bromo-6-chloro-2-(1H-indazol-1-yl)pyrimidine-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vigorously stirring suspension of 2 g (7.4 mmol) of 5-bromo-6-chloro-2-(methylsulfinyl)pyrimidine-4-amine (intermediate 3) in 40 ml of DMF, 0.87 g (7.4 mmol) indazole and 1.4 g (4.4 mmol) of cesium carbonate were added. The reaction mixture was stirred at room temperature for 20 minutes. The solution was poured onto 200 ml of ice-water. The resulting precipitate was filtered, washed with cold water and dried. The desired product is obtained as a white solid 1.31 g (54.6%)

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at room temperature for 20 minutes
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-23f4826a7a51422ba90abdbedf459d76
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447095B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes