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Basic Information
CAS No.: 29569-30-0
Name: 5-carbamoylmethyluridine
Article Data: 9
Molecular Structure:
Molecular Structure of 29569-30-0 (5-carbamoylmethyluridine)
Formula: C11H15 N3 O7
Molecular Weight: 301.256
Synonyms: 5-Pyrimidineacetamide,1,2,3,4-tetrahydro-2,4-dioxo-1-b-D-ribofuranosyl- (8CI); 5-Carbamoylmethyluridine; 5-Uridineacetamide
Density: 1.653g/cm3
Boiling Point: °Cat760mmHg
Flash Point: °C
PSA: 169.12000
LogP: -2.26210
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Synthetic route
957-77-7

5-Hydroxy-uridin

38821-11-3

2-(triphenylphosphoranylidene)acetamide

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
In 1,4-dioxane Heating;99%
20299-15-4

2-thio-5-<(methylcarboxy)methyl>uridine

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
With ammonium hydroxide In water at 25℃; for 18h; Substitution;75%
29428-50-0

5-<(methylcarboxy)methyl>uridine

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
With ammonium hydroxide Ambient temperature;61.6%
With ammonia In methanol for 48h;
With ammonia In methanol for 48h;
With ammonia In methanol at 20℃; for 48h;
With ammonium hydroxide In methanol at 20℃;
58-96-8

uridine

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: pyridine / 3 h / 60 °C
2: acetic anhydride; acetic acid; bromine / 0 - 20 °C
3: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
5: sodium methylate / methanol / 16 h / 50 °C
6: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 6 steps
1: pyridine / 3 h / 60 °C
2: bromine; acetic anhydride; acetic acid / 0 - 20 °C / Sealed tube
3: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
5: sodium methylate; methanol / 16 h / 50 °C
6: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 6 steps
1: pyridine / 3 h / 60 °C
2: bromine; acetic anhydride / acetic acid / 0 - 20 °C / Sealed tube
3: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
5: sodium methylate / methanol / 16 h / 50 °C
6: ammonia / methanol / 48 h / 20 °C
View Scheme
4105-38-8

Tri-O-acetyluridine

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic anhydride; acetic acid; bromine / 0 - 20 °C
2: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
4: sodium methylate / methanol / 16 h / 50 °C
5: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 5 steps
1: bromine; acetic anhydride; acetic acid / 0 - 20 °C / Sealed tube
2: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
4: sodium methylate; methanol / 16 h / 50 °C
5: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 5 steps
1: bromine; acetic anhydride / acetic acid / 0 - 20 °C / Sealed tube
2: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
4: sodium methylate / methanol / 16 h / 50 °C
5: ammonia / methanol / 48 h / 20 °C
View Scheme
105659-31-2, 105659-32-3

5-bromo-2’,3’,5’-tri-O-acetyluridine

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
3: sodium methylate / methanol / 16 h / 50 °C
4: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
3: sodium methylate; methanol / 16 h / 50 °C
4: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 4 steps
1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
3: sodium methylate / methanol / 16 h / 50 °C
4: ammonia / methanol / 48 h / 20 °C
View Scheme
1261157-39-4

5-bromo-N3-benzoyl-2’,3’,5’-tri-O-acetyluridine

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
2: sodium methylate / methanol / 16 h / 50 °C
3: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 3 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
2: sodium methylate; methanol / 16 h / 50 °C
3: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 3 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
2: sodium methylate / methanol / 16 h / 50 °C
3: ammonia / methanol / 48 h / 20 °C
View Scheme
1261157-40-7

N3-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester

29569-30-0

5-(carbamoylmethyl)uridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium methylate / methanol / 16 h / 50 °C
2: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate; methanol / 16 h / 50 °C
2: ammonia / methanol / 48 h
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / methanol / 16 h / 50 °C
2: ammonia / methanol / 48 h / 20 °C
View Scheme
15715-58-9

triethylamine carbonate

29569-30-0

5-(carbamoylmethyl)uridine

5-carbamoylmethyluridine-TP tetrakistriethylammonium salt

Conditions
ConditionsYield
Stage #1: 5-(carbamoylmethyl)uridine With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h;
Stage #2: With trichlorophosphate for 2h; Inert atmosphere;
Stage #3: triethylamine carbonate Further stages;		10.52%
15715-58-9

triethylamine carbonate

29569-30-0

5-(carbamoylmethyl)uridine

5-carbamoylmethyl-UTP tetrakis(triethylammonium) salt

Conditions
ConditionsYield
Stage #1: 5-(carbamoylmethyl)uridine With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h;
Stage #2: With trichlorophosphate for 2h; Inert atmosphere;
Stage #3: triethylamine carbonate Further stages;		10.52%
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