2-Phthalimidoethanethiol → 4-Amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine

HRID 34769

Reaktionsgleichung

Reaktionsgleichung von HRID 34769
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]Cl)[N:3]=1.C[O-].[Na+].[SH:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>CO>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:13][CH2:14][CH2:15][N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[N:3]=1

Komponenten

5

Edukt 3

HCID 962482-PhthalimidoethanethiolHCID 10942334Sodium MethoxideHCID 212988272-(Chloromethyl)pyrimidin-4-amine

Produkt 1

HCID 212988184-Amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine, m.p. 131°-133°.

Aufarbeitung

  1. additionafter the addition
  2. customevaporated to dryness
  3. customThe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  4. customthe aqueous phase separated
  5. additionneutralised by the addition of sodium bicarbonate
  6. extractionThe mixture was extracted with ethyl acetate
  7. customthe extracts dried
  8. customevaporated to dryness
  9. customthe residue was recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-fbd6f7d7f7744cde98909ff39f11321c
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762932

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