Methanol → HCID 53789227, compound

HRID 1111433Notes

Reaction equation

HRID 1111433 reaction equation
[C:1]([NH:6][C:7]1[CH:20]=[CH:19][N:10]([C@@H:11]2[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[CH2:12]2)[C:9](=[O:21])[N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:22][O:23][C:24]1[CH:45]=[CH:44][C:27]([C:28](Cl)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1.CO>N1C=CC=CC=1>[C:1]([NH:6][C:7]1[CH:20]=[CH:19][N:10]([C@@H:11]2[O:18][C@H:15]([CH:16]([C:28]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:27]3[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:45][CH:44]=3)[OH:17])[C@@H:13]([OH:14])[CH2:12]2)[C:9](=[O:21])[N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 688503110522-75-3

Product 1

HCID 53789227HCID 53789227, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Conditions

Temperature
0 °C

Procedure

2.5 mmol of compound 5 are dried by successive additions and evaporations of anhydrous pyridine. There is taking up with 25 ml of pyridine, cooling to 0° C. and the addition of 2.75 mmol (1.1 equivalent) of 4,4'-dimethoxy trityl chloride in 25 ml of pyridine at 0° C. The reaction is allowed to continue for 17 hours at 5° C. and then 2 ml of methanol are added to the reaction medium. After 30 minutes, the solvent is expelled with the rotary evaporator and the oily residue taken up by 100 ml of ethyl acetate, followed by washing 3 times with 50 ml of aqueous 5% NaHOO solution and once with 50 ml of bidistilled water. The organic phase is then dried on sodium sulphate and concentrated. By fractionating on a silica gel column, the thus obtained compound 6 is isolated and corresponds to formula (I), in which B is radical of formula (III) derived from cytosine, R1 and R2 are methyl radicals, R3 the 4,4'-dimethoxy trityl radical, R4 a hydrogen atom and R a hydrogen atom.

Workup

  1. waitAfter 30 minutes
  2. customthe solvent is expelled with the rotary evaporator
  3. washby washing 3 times with 50 ml of aqueous 5% NaHOO solution
  4. customThe organic phase is then dried on sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ded20f37db44fcd8702253792b71a5a
Source dataset
uspto-grants-1990_12
Patent number
US04980460

Reaction notes

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