Iodine → HCID 53847170, compound

HRID 1195804Notes

Reaction equation

HRID 1195804 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][N:13]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][C:17](=[O:18])[NH:16][C:14]1=[S:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]N1C(C)(C)CCCC1(C)C.[I:38]I.C(=O)(O)[O-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl.C(O)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][N:13]1[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:19]([I:38])[C:17](=[O:18])[NH:16][C:14]1=[S:15])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 807IodineHCID 516892Sodium BicarbonateHCID 53793435HCID 53793435, compoundHCID 178418821HCID 178418821, compound

Product 1

HCID 53847170HCID 53847170, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

After cooling 35 ml of tetradydrofuran to -70° C., 2.1 g (15 mmol) of 2,2,6,6-tetramethylpiperidine and 15 mmol of n-butyl lithium were successively added thereto to obtain a lithium tetramethylpiperidide solution. Separately, 2.04 g (15 mmol) of 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-6-phenylthiouracil was dissolved in 20 ml of tetrahydrofuran and added dropwise to the said lithium tetramethylpiperidide solution to react for an hour at -70° C. Then, a solution of 3.81 g (15 mmol) of iodine in 20 ml of tetrahydrofuran was further added to the reaction solution while maintaining the reaction temperature at -70° C. to react for an hour. After the completion of the reaction, the reaction solution was added to 0.8 ml of acetic acid, allowed to warm to room temperature and distributed between a chloroform layer and a saturated aqueous solution of sodium bicarbonate. The chloroform layer was concentrated to dryness. The residue was crystallized from petroleum ether to obtain 1.835 g of 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-5-iodo-6-phenylthiouracil (Yield: 62.8%).

Workup

  1. customto react for an hour at -70° C
  2. customto react for an hour
  3. customAfter the completion of the reaction
  4. temperatureto warm to room temperature
  5. concentrationThe chloroform layer was concentrated to dryness
  6. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-ec815ed54ce04ac9924c9b1e6f2e4014
Source dataset
uspto-grants-1992_05
Patent number
US05112835

Reaction notes

Loading…