Methanol → HCID 60204471, compound

HRID 2267355Notes

Reaction equation

HRID 2267355 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]([CH3:10])([CH3:9])[C:7](=[O:11])[NH:6][C:5]1=[O:12].CO.C(N(CC)C(C)C)(C)C.[Br:24][C:25]1[C:26]([C:32]2[S:33][C:34]([Cl:38])=[CH:35][C:36]=2[Br:37])=[N:27][C:28](Cl)=[N:29][CH:30]=1>CC(O)C>[Br:24][C:25]1[C:26]([C:32]2[S:33][C:34]([Cl:38])=[CH:35][C:36]=2[Br:37])=[N:27][C:28]([NH:1][CH2:2][CH2:3][N:4]2[C:8]([CH3:9])([CH3:10])[C:7](=[O:11])[NH:6][C:5]2=[O:12])=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 57428834HCID 57428834, compound

Product 1

HCID 60204471HCID 60204471, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

A 10% (w/v) solution of 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione in MeOH (4.3 mL, 2.5 mmol) was added to a 10 mL microwave vessel. The MeOH was evaporated with a stream of N2, to leave an oily solid which was dissolved in 0.58 mL (3.3 mmol) of N,N-diisopropylethylamine and 5 mL of iPrOH, to which was added 0.65 g (1.7 mmol) of 5-bromo-4-(3-bromo-5-chlorothiophen-2-yl)-2-chloropyrimidine. The reaction mixture was heated in a microwave to 170° C. for 20 min then concentrated in vacuo and purified by flash chromatography eluting with a linear gradient of 60% EtOAc in hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 524.

Workup

  1. customThe MeOH was evaporated with a stream of N2
  2. customto leave an oily solid which
  3. concentrationthen concentrated in vacuo
  4. custompurified by flash chromatography
  5. washeluting with a linear gradient of 60% EtOAc in hexane to neat EtOAc

Sources & evidence

ORD record
ord-b024744ab1214432af7b2e542be7e883
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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