Chloroform → HCID 60204503, compound

HRID 2267381Notes

Reaction equation

HRID 2267381 reaction equation
[Br:1][C:2]1[C:3]([C:9]2[S:13][C:12]([CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:15][Si](C)(C)C)=[N:11][CH:10]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:26][CH2:27][CH2:28][N:29]1[C:33]([CH3:35])([CH3:34])[C:32](=[O:36])[NH:31][C:30]1=[O:37].C(N(CC)C(C)C)(C)C.C(Cl)(Cl)Cl.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC(O)C.C1COCC1>[Br:1][C:2]1[C:3]([C:9]2[S:13][C:12]([CH:14]([OH:15])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:11][CH:10]=2)=[N:4][C:5]([NH:26][CH2:27][CH2:28][N:29]2[C:33]([CH3:34])([CH3:35])[C:32](=[O:36])[NH:31][C:30]2=[O:37])=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 6212ChloroformHCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 60204504HCID 60204504, compound

Product 1

HCID 60204503HCID 60204503, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 150 mg (0.33 mmol) of 5-bromo-2-chloro-4-{2-[phenyl(trimethylsilyloxy)-methyl]-thiazol-5-yl}pyrimidine, 85 mg (0.50 mmol) of 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione and N,N-diisopropylethylamine (0.17 mL, 0.99 mmol) in 4 mL of iPrOH and 1 mol of CHCl3 was heated in a microwave to 170° C. for 20 min and then treated with 0.75 mL of a 1 M solution of tetra-n-butylammonium fluoride in THF for 10 min at rt. The reaction solution was concentrated in vacuo and the crude solid product was purified by flash chromatography eluting with a linear gradient of 75% EtOAc in hexane to 100% EtOAc to deliver the title compound. MS (M+H)+ 519.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe crude solid product was purified by flash chromatography
  3. washeluting with a linear gradient of 75% EtOAc in hexane to 100% EtOAc

Sources & evidence

ORD record
ord-154aa0116835448b89ac67eb47a28d26
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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