Diisopropylamine → 2-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide

HRID 453376

反応式

HRID 453376 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C.[N:45]1[CH:50]=[C:49]([NH2:51])[CH:48]=[N:47][CH:46]=1>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:51][C:49]1[CH:50]=[N:45][CH:46]=[N:47][CH:48]=1)=[O:6]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 344373Pyrimidin-5-amineHCID 5196832-Methyl-5-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 248232552-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a 2L round bottom flask with mechanical stirring was charged with 2-methyl-5-nitrobenzoic acid (20 g), HATU (38 g) and diisopropylamine (32 mL) in DMF (90 mL). This mixture was stirred for 30 min then pyrimidin-5-amine was added and the reaction was stirred for 18 hr. The LCMS showed complete conversion. DMF was removed under vacuum as much as possible then water was added and a solid precipitated out (use mechanical stirring). The tan solid was filtered and rinsed with water, then taken up in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated down. The crude was taken up in EtOAc and the product 45 precipitated out. This was filtered and the filtrate was concentrated down and taken up in EtOAc/Hex. After standing overnight, more solids were filtered and were combined with the first crop. 2-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide 45 was obtained as a light yellow solid.

後処理

  1. stirringthe reaction was stirred for 18 hr
  2. customDMF was removed under vacuum as much as possible then water
  3. additionwas added
  4. customa solid precipitated out
  5. stirring(use mechanical stirring)
  6. filtrationThe tan solid was filtered
  7. washrinsed with water
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated down
  12. customthe product 45 precipitated out
  13. filtrationThis was filtered
  14. concentrationthe filtrate was concentrated down
  15. waitAfter standing overnight
  16. filtrationmore solids were filtered

出典と根拠

ORDレコード
ord-8412d5d5f20e47908513066372e957b3
出典データセット
uspto-grants-2013_07
特許番号
US08492404B2

関連ノート

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