Diisopropylethylamine → Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate

HRID 1946680

反応式

HRID 1946680 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.ClC1N=CN=C(C(NC2C=CC(O)=CC=2)=O)C=1.[C:28]([O:32][C:33](=[O:43])[NH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)([CH3:31])([CH3:30])[CH3:29].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:42][C:39]2[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:33](=[O:43])[O:32][C:28]([CH3:30])([CH3:31])[CH3:29])=[CH:37][CH:38]=2)=[O:9])[CH:3]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

生成物 1

HCID 59447092Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a cooled (0° C.) solution of 6-chloropyrimidine-4-carbonyl chloride in DCM (30 mL), obtained as described above for Intermediate 7, step 1 (1.43 g; 8.10 mmol) was added dropwise, during a period of 15 minutes, a solution of (4-amino-benzyl)-carbamic acid tert-butyl ester (Astatech, 1.50 g; 6.75 mmol) and DIEA (2.33 ml; 13.5 mmol) in DCM (5 mL). At the end of addition the reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. The resulting precipitate was filtered and dried under vacuum. The mother liquors were dried on MgSO4, concentrated under vacuum to give a residue, which was precipitated from cyclohexane. The two solids were combined to give the title compound as a brown solid.

後処理

  1. customobtained
  2. additionwas added dropwise, during a period of 15 minutes
  3. additionAt the end of addition the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted with EtOAc
  7. filtrationThe resulting precipitate was filtered
  8. customdried under vacuum
  9. customThe mother liquors were dried on MgSO4
  10. concentrationconcentrated under vacuum
  11. customto give a residue, which
  12. customwas precipitated from cyclohexane

出典と根拠

ORDレコード
ord-88b2f155075c41a8b77e561f108d2152
出典データセット
uspto-grants-2013_03
特許番号
US08399448B2

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