Triethylamine → HCID 18791912, compound

HRID 1005435Notes

Reaction equation

HRID 1005435 reaction equation
O.[OH:2][CH2:3][C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1.C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([C:25](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1>N1C=CC=CC=1>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]([O:2][CH2:3][C:4]2[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:24]2[CH:41]=[CH:42][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 16218595HCID 16218595, compound

Product 1

HCID 18791912HCID 18791912, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

5-(Hydroxymethyl)-uracil hydrate 1 (10.00 gm, 0.070 moles) is co-evaporated three times with 50 ml dry pyridine and dissolved in 200 ml dry pyridine at room temperature. Triethylamine (9.8 ml, 0.070 moles) and 4,4'-dimethoxytrityl chloride (23.7 gm, 0.070 moles) are added and the mixture is stirred for 6 hours under a nitrogen atmosphere. Most of the pyridine is removed under reduced pressure and the residue is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase is washed twice with saturated sodium chloride, dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The oily residue is triturated with ethyl acetate and hexane to give 5-(4,4'-dimethoxytrityloxymethyl)-uracil 2 as an off-white solid.

Workup

  1. customMost of the pyridine is removed under reduced pressure
  2. customthe residue is partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic phase is washed twice with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe oily residue is triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-234740ecea654636aef9d029570212b3
Source dataset
uspto-grants-2000_04
Patent number
US06054568

Reaction notes

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