Potassium Carbonate → HCID 67459801, compound

HRID 2192204Notes

Reaction equation

HRID 2192204 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4](Cl)[N:3]=1.[CH3:10][C@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([CH3:20])=[CH:16][CH:17]=2)[C@@H:12]1[NH2:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Br:8][C:7]1[C:2]([NH2:1])=[N:3][C:4]([NH:21][C@H:12]2[C:13]3[C:18](=[CH:17][CH:16]=[C:15]([CH3:20])[CH:14]=3)[CH2:19][C@@H:11]2[CH3:10])=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27632934-Amino-5-bromo-2-chloropyrimidineHCID 671406111351564-23-2

Product 1

HCID 67459801HCID 67459801, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.2 g (0.96 mmol) of 4-amino-5-bromo-2-chloropyrimidine, 0.196 g (1.15 mmol) of (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-amine and 0.399 g of potassium carbonate are heated in 1.5 ml of N,N-dimethylacetamide at 170° C. in a closed cell in a microwave for 60 minutes (Biotage initiator, http://www.biotage.com/DynPage.aspx?id=22001). The resulting crude mixture is absorbed on silica gel and purified by means of column chromatography using heptane/ethyl acetate as eluent. Following concentration by evaporation, 0.13 g of 5-bromo-N2-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]pyrimidine-2,4-diamine is obtained (yield 37% at 95% purity).

Workup

  1. customThe resulting crude mixture is absorbed on silica gel
  2. custompurified by means of column chromatography
  3. concentrationconcentration
  4. customby evaporation

Sources & evidence

ORD record
ord-bae6cd209e8e4bdf83b11add1fd1262e
Source dataset
uspto-grants-2012_12
Patent number
US08329717B2

Reaction notes

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