3,4,5,6-Tetrahydrouridine → 18771-50-1

HRID 328549Notes

Reaction equation

HRID 328549 reaction equation
[C@@H:1]1([N:10]2[CH2:17][CH2:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[BH4-].[Na+]>O>[OH:15][CH:14]1[CH2:16][CH2:17][N:10]([C@@H:1]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]2[OH:3])[C:11](=[O:12])[NH:13]1

Participants

4

Reactant 2

HCID 943123,4,5,6-TetrahydrouridineHCID 4311764Sodium borohydride

Product 1

HCID 2924318771-50-1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of 246.2 mg. (1.0 mmole) of 5,6-dihydrouridine in 10 ml. of water at pH 7.5-8 was added 37.8 mg. (1.0 mmole-4.0 equivalents) of sodium borohydride. After 35 minutes the reaction mixture was set in a freezer overnight and put into an ice bath the next morning. The excess sodium borohydride was destroyed by addition of dilute acetic acid, the mixture was filtered and the filtrate lyophilized to give 4-hydroxy-1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone and a small amount of 1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone.

Workup

  1. customput into an ice bath
  2. customThe excess sodium borohydride was destroyed by addition of dilute acetic acid
  3. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-086dec79d6984831a5909197b7d7ca6b
Source dataset
uspto-grants-1977_04
Patent number
US04017606

Reaction notes

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