Ethylene Glycol → 4-Methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide

HRID 1181238

Reaktionsgleichung

Reaktionsgleichung von HRID 1181238
[CH3:1][O:2][CH2:3][CH2:4][O:5]C.C(O)CO.[Na].ClC1[N:18]=[CH:17][N:16]=[C:15]([NH:19][S:20](=[O:30])(=[O:29])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[C:14]=1[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1>CN(C=O)C>[OH:5][CH2:4][CH2:3][O:2][C:1]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][S:20](=[O:29])(=[O:30])[NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[C:14]=1[C:31]1[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 80711,2-DimethoxyethaneHCID 5360545Sodium2×HCID 219795524-Methyl-phenyl sulfamic acid-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-amide

Produkt 1

HCID 219795764-Methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1,2-dimethoxyethan (15 ml) and ethyleneglycol (40 ml) was added sodium (298 mg) in small portions. The mixture was stirred until the sodium was completely dissolved. Then DMF (15 ml), followed by 4-methyl-phenyl sulfamic acid-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-amide (1.0 g, Referential Example 14) was added. Stirring was continued for 4 days at 100° C. The mixture was evaporated and water (150 ml) was added to the residue followed by addition of acetic acid (1.0 ml). The precipitate was filtered off, washed with water and dried. The crude material was purified by chromatography over silicagel with EtOAc/methanol/aquous ammonia (25%)=4/1/0.5 to give 4-methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide (500 mg). tR=4.38 (LC); [M+H]+=415.19 (ES+).

Aufarbeitung

  1. dissolutionwas completely dissolved
  2. additionwas added
  3. customThe mixture was evaporated
  4. additionwater (150 ml) was added to the residue
  5. additionfollowed by addition of acetic acid (1.0 ml)
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customThe crude material was purified by chromatography over silicagel with EtOAc/methanol/aquous ammonia (25%)=4/1/0.5

Quellen und Nachweise

ORD-Eintrag
ord-0d0d1629cb054d47bbdc6e0ad4512b34
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285549B2

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