Sodium Nitrite → 5'-(3-Methyl-3-nitrosoureido)-5'-deoxythymidine

HRID 65659Notes

Reaction equation

HRID 65659 reaction equation
[CH3:1][NH:2][C:3](=[O:21])[NH:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[OH:20].[N:22]([O-])=[O:23].[Na+]>C(O)(=O)C>[CH3:1][N:2]([N:22]=[O:23])[C:3](=[O:21])[NH:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[OH:20]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 540012745'-(3-Methylureido)-5'-deoxythymidine

Product 1

HCID 541182865'-(3-Methyl-3-nitrosoureido)-5'-deoxythymidineYield 70.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4 (1.00 g, 3.35 mmol) in 50% aqueous acetic acid at 0°, sodium nitrite (0.31 g, 4.55 mmol) was added slowly. The reaction mixture was kept at 0° with stirring for 3 h, during which time crystals started to precipitate out. The product was collected by filtration, washed with water, cooled methanol, ether, and dried. The filtrate was concentrated and an additional fraction of crystals was obtained. The combined product was recrystallized from methanol to yield 0.77 g (70%) of white fine needles: mp 159°-160° dec.: uvλmaxEtOH 264 nm (ε11,000); uvλminEtOH 235 nm. Anal. (C12H17N5O6) C, H, N.

Workup

  1. customwas kept at 0°
  2. customto precipitate out
  3. filtrationThe product was collected by filtration
  4. washwashed with water
  5. temperaturecooled methanol, ether
  6. customdried
  7. concentrationThe filtrate was concentrated
  8. customan additional fraction of crystals was obtained
  9. customThe combined product was recrystallized from methanol

Sources & evidence

ORD record
ord-678d938fe117450c94947b855d5556e4
Source dataset
uspto-grants-1978_12
Patent number
US04128639

Reaction notes

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