methyl 1-uracil-5-carboxylate

Base Information

• Chemical Name: methyl 1-uracil-5-carboxylate
• CAS No.: 111690-20-1
• Molecular Formula: C₂₉H₂₈N₂O₁₁
• Molecular Weight: 580.548

Synonyms:

Chemical Property of methyl 1-uracil-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl 1-uracil-5-carboxylate

There total 12 articles about methyl 1-uracil-5-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzoyl chloride (98-88-4) → methyl 1-uracil-5-carboxylate (111690-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / pyridine / 1 h

2: 77 percent / SeO₂, HOAc / dioxane / 0.75 h / Heating

3: Jones' reagent / acetone / 0.5 h

4: HCl / 0.83 h / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; jones' reagent; acetic acid; In 1,4-dioxane; acetone;

DOI:10.1021/jo00237a011

Reference yield:

methyl 2,4-dihydroxypyrimidine-5-carboxylate (42821-92-1) → methyl 1-uracil-5-carboxylate (111690-20-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.25 h / Heating

2: Me₃SiOSO₂CF₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: sodium methoxide / methanol / 1 h / Ambient temperature

4: p-toluenesulfonic acid / dimethylformamide / 12 h / Ambient temperature

5: pyridine / 0.5 h

6: 90percent aq. trifluoroacetic acid / 0.5 h / Ambient temperature

7: 1.) NaH 2.) HCl / 1.) DMSO, 50 deg C, 2.5 h, 2.) MeOH, reflux, 0.5 h

8: 86 percent / pyridine / 1 h

9: 77 percent / SeO₂, HOAc / dioxane / 0.75 h / Heating

10: Jones' reagent / acetone / 0.5 h

11: HCl / 0.83 h / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; jones' reagent; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00237a011

Reference yield:

methyl 1-<8-O-allyl-3,7-anhydro-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate (111690-17-6) → methyl 1-uracil-5-carboxylate (111690-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / pyridine / 1 h

2: 77 percent / SeO₂, HOAc / dioxane / 0.75 h / Heating

3: Jones' reagent / acetone / 0.5 h

4: HCl / 0.83 h / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; jones' reagent; acetic acid; In 1,4-dioxane; acetone;

DOI:10.1021/jo00237a011

upstream raw materials:

methanol

benzoyl chloride

methyl 2,4-dihydroxypyrimidine-5-carboxylate

methyl 1-<8-O-allyl-3,7-anhydro-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

Downstream raw materials:

1-((2R,3R,3aS,7R,7aR)-5-Carboxy-3,7-dihydroxy-hexahydro-furo[3,2-b]pyran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid

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