2,4-Diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidine → 2,4-diamino-5-(7,8-dimethoxy-2-methyl-2H-1-benzopyran-5-ylmethyl)pyrimidine

HRID 34453

Reaktionsgleichung

Reaktionsgleichung von HRID 34453
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH:17]([CH3:20])[C:18]#[CH:19])[C:13]([O:21][CH3:22])=[C:12]([O:23][CH3:24])[CH:11]=2)=[CH:4][N:3]=1>C(N(CC)C1C=CC=CC=1)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[CH:19]=[CH:18][CH:17]([CH3:20])[O:16][C:14]=3[C:13]([O:21][CH3:22])=[C:12]([O:23][CH3:24])[CH:11]=2)=[CH:4][N:3]=1

Komponenten

3

Edukt 1

HCID 128498022,4-Diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidine

Produkt 1

HCID 128497982,4-diamino-5-(7,8-dimethoxy-2-methyl-2H-1-benzopyran-5-ylmethyl)pyrimidineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7061N,N-DiethylanilineLösungsmittel

Versuchsvorschrift

A solution of 2,4-diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidine (4.28 g, 13.0 mmol) in N,N-diethylaniline (200 mL) was refluxed under nitrogen for 0.5 hr. The hot solution was filtered to remove dark tarry material. The filtrate was cooled and diluted with hexanes (200 mL). The precipitate (3.8 g) was recrystallized from ethanol to give title compound as off-white powder (1.56 g, 37%); mp 219°-221° dec. Anal. Calcd for C17H20N4O3 : C, 62.18; H, 6.14; N, 17.06. Found: C, 61.91; H, 6.20; N, 16.93.

Aufarbeitung

  1. filtrationThe hot solution was filtered
  2. customto remove dark tarry material
  3. temperatureThe filtrate was cooled
  4. additiondiluted with hexanes (200 mL)
  5. customThe precipitate (3.8 g) was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ff7dd95dab7f4c838340ddf80907f226
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761475

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