Dichloromethane → HCID 178455197, compound

HRID 1637782Notes

Reaction equation

HRID 1637782 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([OH:11])[N:5]=[C:4]([S:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[N:3]=1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C(Cl)Cl>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][O:10][Si:24]([CH3:26])([CH3:25])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:6]([OH:11])[N:5]=[C:4]([S:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 178509035HCID 178509035, compound

Product 1

HCID 178455197HCID 178455197, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-amino-6-hydroxy-2-[2-naphthylmethyl]thio-5-pyrimidinyl)-ethanol (Cpd #279; 106 mg, 0.32 mmol) is dissolved in pyridine (0.64 ml) and the solution is cooled to 0° C. then treated with t-butyl dimethylsilyl chloride (0.058 g, 0.39 mmol). The solution is stirred at 0° C. for 2 hours and two new spots developed in the mixture. The reaction mixture is poured into methylene chloride and washed 3× with 1 M HCl, 10% HCl, 3× H2O, 2× 6% NaHCO3, dried with MgSO4, then concentrated in vacuo. The crude product is then purified by chromatography (SiO2 1:1 hexane/ethyl acetate): 60 mg (0.18 mmol, 57%), mp 156-158° C.

Workup

  1. washwashed 3× with 1 M HCl, 10% HCl, 3× H2O, 2× 6% NaHCO3
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is then purified by chromatography (SiO2 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc6385b2b3e4431bb07f748cd87eef7b
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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