Water → 5-bromo-6-chloro-2-(1H-indazol-1-yl)-N-(prop-2-ynyl)pyrimidine-4-amine

HRID 63608

Reaction equation

HRID 63608 reaction equation
[Br:1][C:2]1[C:3]([NH:12][CH2:13][C:14]#[CH:15])=[N:4][C:5](S(C)=O)=[N:6][C:7]=1[Cl:8].[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[N:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[Br:1][C:2]1[C:3]([NH:12][CH2:13][C:14]#[CH:15])=[N:4][C:5]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 92211H-IndazoleHCID 10796Cesium carbonateHCID 903037735-bromo-6-chloro-2-(methylsulfinyl)-N-(prop-2-ynyl)pyrimidine-4-amine2×

Product 1

HCID 903037695-bromo-6-chloro-2-(1H-indazol-1-yl)-N-(prop-2-ynyl)pyrimidine-4-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 0.5 g (1.62 mmol) of 5-bromo-6-chloro-2-(methylsulfinyl)-N-(prop-2-ynyl)pyrimidine-4-amine (intermediate 31) in 2 ml of DMSO, 0.19 g (1.62 mmol) indazole and 0.32 g of cesium carbonate were added. The slightly yellow solution was stirred at room temperature for 20 minutes. The reaction mixture was poured onto 10 ml of cold water. The resulting precipitate was filtered, washed with cold water and dried. The desired product was obtained as a white solid 0.31 g (52.8%).

Workup

  1. additionwere added
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-72ce7ae0ea644282b459e72d34d41508
Source dataset
uspto-grants-2016_09
Patent number
US09447095B2

Linked notes

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