Aniline → HCID 86630086, compound

HRID 1365833Notes

Reaction equation

HRID 1365833 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9](S(C)(=O)=O)=[N:8][C:6]=2[N:7]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 576854065-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine

Product 1

HCID 86630086HCID 86630086, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine (1.0 eq) and aniline (1.0 eq) were heated in toluene at 60° C. for 15 h. Upon completion, reaction mixture was concentrated in vacuo and crude mixture was purified by silica gel chromatography to give intermediate 5-chloro-7-morpholino-N-phenylthiazolo[4,5-d]pyrimidin-2-amine which was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (2.0 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.10 eq) in 1M KOAc aqueous solution (3.0 eq) and a 4× volume of acetonitrile and heated to 150° C. in a sealed microwave reactor for 10 min. Upon completion, reaction mixture was concentrated in vacuo and crude mixture was purified by silica gel chromatography to give 146. MS (Q1) 406 (M)

Workup

  1. customUpon completion, reaction mixture
  2. concentrationwas concentrated in vacuo and crude mixture
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-722527fa49b14ef58ca6fd89b2b76b5e
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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