Hydrochloric Acid → Ethyl ({4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}oxy)acetate

HRID 657093Notes

Reaction equation

Cl.[NH2:2][C:3]1[C:8]([O:9][CH2:10][C:11](N)=[O:12])=[C:7]([Cl:14])[N:6]=[C:5](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1.[CH2:23]([OH:25])[CH3:24]>>[NH2:2][C:3]1[C:8]([O:9][CH2:10][C:11]([O:25][CH2:23][CH3:24])=[O:12])=[C:7]([Cl:14])[N:6]=[C:5](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 866353532-({4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}oxy)acetamide

Product 1

HCID 57928064Ethyl ({4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}oxy)acetateYield 84%

Conditions

Temperature: 100 °C

Procedure

Hydrogen chloride gas was bubbled into a solution of 2-({4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}oxy)acetamide (0.6 g, 1.97 mmol) in ethanol (20 mL). The resulting mixture was heated at 100° C. for 3 h. The mixture was evaporated under reduced pressure to give the desired product as a solid (0.55 g, 84%) which was used without purification.

Workup

customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record: ord-165af224578642759cd082e89465ff24
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

Loading…