Diisopropylethylamine → 3-(2-Chloropyrimidin-5-yl)-5,5-dimethyl-imidazolidine-2,4-dione

HRID 1484643ノート

反応式

HRID 1484643 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[N:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=1.CCN(C(C)C)C(C)C.Cl.C[O:32][C:33](=O)[C:34]([CH3:37])([CH3:36])[NH2:35]>C(OCC)(=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.ClCCl>[Cl:13][C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:33](=[O:32])[C:34]([CH3:37])([CH3:36])[NH:35][C:5]2=[O:11])=[CH:16][N:15]=1

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 122159932-Chloropyrimidin-5-amineHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

生成物 1

HCID 866984523-(2-Chloropyrimidin-5-yl)-5,5-dimethyl-imidazolidine-2,4-dione

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒3 回HCID 21226138Dichloromethane ethylacetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of triphosgene (1.38 g, 4.65 mmol) in Ethyl acetate (20 ml) at 0° C. a solution of 2-chloro-5-aminopyrimidine (1 g, 7.75 mmol)/DIPEA (8 ml, 4.65 mmol) in ethyl acetate (40 ml) was slowly added (20 minutes) and the reaction mixture was stirred for 15 minutes at the same temperature. Maintaining the reaction mixture at 0° C., vacuum was applied (10 minutes) for removing the excess of phosgene. A solution of DMAP (0.945 g, 7.75 mmol) in ethyl acetate/dichloromethane 1:1 (8 ml) was added and the reaction mixture was stirred for 5 minutes at the same temperature. 2,2-Dimethylglycine methyl ester hydrochloride (2.37 g, 15.5 mmol) in ethyl acetate (30 ml) was slowly added (15 minutes) at 0° C. and the reaction mixture was stirred for 30 minutes at the same temperature. The reaction was quenched with aqueous buffer (pH3) while the pH was allowed to reach ˜5-6 and two phases were separated. The organic layer was washed with aqueous buffer (pH3) (2×20 ml) and then brine (20 ml), dried (Na2SO4), filtered and evaporated affording the urea intermediate as orange foam.

後処理

  1. custom(10 minutes)
  2. customfor removing the excess of phosgene
  3. stirringthe reaction mixture was stirred for 5 minutes at the same temperature
  4. stirringthe reaction mixture was stirred for 30 minutes at the same temperature
  5. customThe reaction was quenched with aqueous buffer (pH3) while the pH
  6. customwere separated
  7. washThe organic layer was washed with aqueous buffer (pH3) (2×20 ml)
  8. dry with materialbrine (20 ml), dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-2cf15385a09848028bfbfb1813015550
出典データセット
uspto-grants-2016_08
特許番号
US09422272B2

反応ノート

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