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

HRID 65660Notes

Reaction equation

HRID 65660 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[CH3:18][N:19]=[C:20]=[O:21]>CO>[CH3:18][NH:19][C:20](=[O:21])[NH:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 1080743'-Aminothymidine

Product 1

HCID 545281063'-(3-Methylureido)-3'-deoxythymidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7 (0.48 g, 2.00 mmol) in 15 ml of methanol, methyl isocyanate (0.13 g, 2.20 mmol) was added slowly. The solution was stirred at 0° for 1 h, during which period, white crystals precipitated out. The product was collected by filtration, washed with cooled methanol, and dried, to give 0.54 g (90%). The compound softened at 114° and effervesced at 120°; TLC: Rf 0.38. Anal. (C12H18N4O5) C, H, N.

Workup

  1. customprecipitated out
  2. filtrationThe product was collected by filtration
  3. washwashed with cooled methanol
  4. customdried
  5. customto give 0.54 g (90%)
  6. customsoftened at 114°
  7. customeffervesced at 120°

Sources & evidence

ORD record
ord-c3edb58f4c2b480fab7f88306aa4fa57
Source dataset
uspto-grants-1978_12
Patent number
US04128639

Reaction notes

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