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Sulfuric Acid → HCID 178497740, Verbindung

HRID 2350866
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2350866
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].NC(N)=N.[C:13]([CH:18]([C:33]#[N:34])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)(OCC)=[O:14].S(=O)(=O)(O)O>CN(C)C=O.CO>[NH2:4][C:3]1[N:5]=[C:33]([NH2:34])[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)=[C:13]([OH:14])[N:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 14796094HCID 14796094, Verbindung

Produkt 1

HCID 178497740HCID 178497740, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.71 g (1.05 eq) of guanidine hydrochloride, 0.40 g (1.05 eq) of sodium methoxide, and 20 mL of anhydrous methanol is stirred under nitrogen for 30 minutes. The solid which forms is removed by filtration and the filtrate concentrated under reduced pressure. To the residue (guanidine free base) is added 2.15 g (1.0 eq) of methyl 4-(5-carbethoxy-5-cyanopentyl)benzoate in 20 mL of anhydrous dimethylformamide. This mixture is stirred under nitrogen with gentle heating for 12 hours, cooled, and then mixed with very dilute sulfuric acid. The solid is collected, washed with water and then diethyl ether, and dried to yield methyl 4-[4-(2,4-diamino-6-hydroxypyrimidin-5-yl)butyl]-benzoate, m.p. 203°-205° C.; IR (KBR) vmax 3495, 3380, 2925, 2850, 1685, 1600, 1490, 1430, 1359, 1282, 1174, 1111, 1015, and 754 cm-1 ; 1H NMR (d6DMSO) delta 9.74 (bs, 1H (3)--NH), 7.83 (d, J=8.1 Hz, 2H, Ar), 7.31 (d, J=8.1 Hz, 2H, Ar), 5.87 (bs, 2H (2)--NH2), 5.60 (bs, 2H, (6)--NH2), 3.80 (s, 3H, CH3), 2.62 (t, J=7.6 Hz, 2H, (5)--CH2), 2.15 (t, J=7.2 Hz, 2H, benzyl), 1.51-1.55 (m, 2H, 2° aliphatic), 1.26-1.28 (m, 2H 2° aliphatic).

Aufarbeitung

  1. customThe solid which forms is removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. stirringThis mixture is stirred under nitrogen
  4. temperaturewith gentle heating for 12 hours
  5. temperaturecooled
  6. customThe solid is collected
  7. washwashed with water
  8. dry with materialdiethyl ether, and dried

Quellen und Nachweise

ORD-Eintrag
ord-122db312600f4fe49505d25241da49a6
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04871743

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