Acetic Acid → 1-[(2-t-Butyldimethylsilyloxyethoxy)methyl]-5-ethyl-6-phenylthio-2-thiouracil

HRID 1109078Notes

Reaction equation

HRID 1109078 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[Si:9]([O:16][CH2:17][CH2:18][O:19][CH2:20][N:21]1[CH:28]=[C:27]([CH2:29][CH3:30])[C:25](=O)[NH:24][C:22]1=[S:23])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C1([S:37]SC2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.O1C[CH2:52][CH2:51][CH2:50]1>>[Si:9]([O:16][CH2:17][CH2:18][O:19][CH2:20][N:21]1[C:28]([C:6]2[CH:5]=[CH:7][CH:52]=[CH:51][CH:50]=2)=[C:27]([CH2:29][CH3:30])[C:25](=[S:37])[NH:24][C:22]1=[S:23])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 8028Tetrahydrofuran4×HCID 13436Diphenyl disulfideHCID 2724682Lithium diisopropylamideHCID 106892291-[(2-t-Butyldimethylsilyloxyethoxy)methyl]-5-ethyl-2-thiouracil

Product 1

HCID 190216511-[(2-t-Butyldimethylsilyloxyethoxy)methyl]-5-ethyl-6-phenylthio-2-thiouracilYield 76%

Conditions

Temperature
-70 °C

Procedure

Next, 11 ml (22 mmol) of 2.0M solution of lithium diisopropylamide in tetrahydrofuran was added under a nitrogen atmosphere to 30 ml of tetrahydrofuran which has been cooled down to -70° C. in advance. To this was added dropwise 14 ml of tetrahydrofuran solution containing 3.4 g (10 mmol) of the thus obtained 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-5-ethyl-2-thiouracil by keeping the reaction solution at a temperature of -70° C. or lower. The resulting mixture was stirred for 1 hour at -70° C. To this was added dropwise 10 ml of tetrahydrofuran solution containing 2.8 g (13 mmol) of diphenyl disulfide. After 1 hour, the resulting reaction mixture was further mixed with 1.3 ml of acetic acid, adjusted to room temperature and subjected to partition using an ethyl acetate-water system, and then the organic layer was evaporated to dryness. Thereafter, the residue was adsorbed on a silica gel column and eluted with chloroform to obtain 3.4 g (76%) of 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-5-ethyl-6-phenylthio-2-thiouracil.

Workup

  1. customat a temperature of -70° C.
  2. waitAfter 1 hour
  3. customthe resulting reaction mixture
  4. customadjusted to room temperature
  5. customto partition
  6. customthe organic layer was evaporated to dryness
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-577b24794147434d89c36fceff3a9a20
Source dataset
uspto-grants-1994_06
Patent number
US05318972

Reaction notes

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