Pyridine → HCID 20525078, compound

HRID 1702806Notes

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH3:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][C:21]([CH2:29]C(O)=O)([CH2:22]3)[CH2:20]1)[CH2:26]2.[N:33]1[CH:38]=CC=CC=1>>[CH3:18][C:19]12[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][C:21]([CH2:29][N:33]=[C:38]=[O:8])([CH2:27]3)[CH2:20]1)[CH2:28]2

Participants

Reactant 3

HCID 1049Pyridine

HCID 85698(3-Methyladamantan-1-yl)acetic acid

HCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 20525078HCID 20525078, compound

Conditions

Temperature: 100 °C

Procedure

Diphenylphosphoryl azide (6.41 g.) was added dropwise to a solution of 3-methyladamantan-1-ylacetic acid (4.85 g.) in dry pyridine (20 ml.) and stirred at 100° C. for 40 minutes to give 3-methyladamantan-1-ylmethyl isocyanate [I.R.: 2260 cm-1 ]. 5-Fluorouracil (2.52 g.) was added to the solution and stirred at 100° C. for 2 hours. The resultant mixture was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with dilute hydrochloric acid and water. Ethyl acetate layer was dried over magnesium sulfate, filtered and evaporated to give residue, which was recrystallized from ethanol to give colorless crystals of 1-[N-(3-methyladamantan-1-ylmethyl)carbamoyl]-5-fluorouracil. (984 mg.)

Sources & evidence

ORD record: ord-a726b5ac3c98428fba29fc467d614109
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04349552

Reaction notes

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