Methyl Isocyanate → 5'-(3-Methylureido)-5'-deoxythymidine

HRID 65658Notes

Reaction equation

HRID 65658 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17].[CH3:18][N:19]=[C:20]=[O:21]>CO.O>[CH3:18][NH:19][C:20](=[O:21])[NH:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 653115'-Amino-5'-deoxythymidine

Product 1

HCID 540012745'-(3-Methylureido)-5'-deoxythymidineYield 72.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 5'-amino-5'-deoxythymidine (2, 2.40 g, 9.95 mmol) in methanol-water (2.5:1, v/v) at 0° was added methyl isocyanate (0.63 g, 10.95 mmol). The reaction mixture was kept at 0° with stirring for 1 h, allowed to warm up to room temperature, and then clarified by filtration. The filtrate was evaporated to dryness under reduced pressure at a temperature not exceeding 35°, and the residue was then crystallized from methanol at 3° overnight to give 2.14 g (72%) of white fine needles: mp 238-239°. Anal. (C12H18N4O5) C, H, N.

Workup

  1. customwas kept at 0°
  2. filtrationclarified by filtration
  3. customThe filtrate was evaporated to dryness under reduced pressure at a temperature not
  4. customexceeding 35°
  5. customthe residue was then crystallized from methanol at 3° overnight

Sources & evidence

ORD record
ord-6b7f654ba604419c81e0b8a9cdee20a6
Source dataset
uspto-grants-1978_12
Patent number
US04128639

Reaction notes

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