* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Farmaco, Edizione Scientifica, 1983, vol. 38, # 4, p. 255 - 264
[2] Bollettino chimico farmaceutico, 2004, vol. 143, # 7, p. 275 - 279
[3] Journal of Organic Chemistry, 1959, vol. 24, p. 922,924
2
[ 14001-64-0 ]
[ 62-53-3 ]
[ 53112-28-0 ]
Reference:
[1] Journal of the Chemical Society, 1946, p. 362,365
3
[ 14001-64-0 ]
[ 35144-22-0 ]
Yield
Reaction Conditions
Operation in experiment
73%
With water; chlorine In dichloromethane at 0℃;
15.9 g (103 mmol) of 4,6-dimethyl-1-methylthiopyrimidine were introduced into 120 ml of dichloromethane and 110 ml of water.. chlorine gas was passed into saturation (yellow coloration) at 0° C. After the conversion was complete, excess chlorine was driven out with nitrogen, the aqueous phase was extracted with dichloromethane, and the collected organic phases were dried over magnesium sulfate.. The solution was concentrated, and the product (14 g, 73percent) was crystallized by adding ether. Melting point: 79-80° C. 1H-NMR (270 MHz): 7.2 ppm (1H, s), 3.4 (3H, s), 2.6 (6H, s).
Reference:
[1] Patent: US6670367, 2003, B1, . Location in patent: Page column 15-16
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2776 - 2795
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-methyl-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-[(1SR,9bSR)-1-(4,6-dimethylpyrimidin-2-yloxy)-2,4-dioxo-9b-phenyl-1,3,4,9b-tetrahydro-2H-2a,5-diazabenzo[a]cyclobuta[c]cyclohepten-5-yl]acetonitrile[ No CAS ]
5-(2-dimethylamino-ethyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-cyclopropylmethyl-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-benzyl-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
9b-(3-butyl-phenyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
9b-biphenyl-3-yl-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-1-(2-hydroxyethyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
acetic acid 2-[1-(4,6-dimethyl-pyrimidin-2-yloxy)-2,4-dioxo-9b-phenyl-1,3,4,9b-tetrahydro-2<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cyclohepten-5-yl]-ethyl ester[ No CAS ]
[1-(4,6-dimethyl-pyrimidin-2-yloxy)-2,4-dioxo-9b-phenyl-1,3,4,9b-tetrahydro-2<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cyclohepten-5-yl]-acetic acid ethyl ester[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-methyl-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(2-methyl-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(2-fluoro-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-[(5SR)-1-(2-dimethylaminoethyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-(4,6-dimethylpyrimidin-2-yloxy)acetic acid[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-phenethyl-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-[(5SR)-1-cyclopropylmethyl-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-(4,6-dimethylpyrimidin-2-yloxy)acetic acid[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-[2-(2-methoxy-ethoxy)-ethyl]-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-hexyl-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(2-chloro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(3-methyl-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(1SR,9bSR)-1-(4,6-dimethylpyrimidin-2-yloxy)-9b-phenyl-5-(1H-tetrazol-5-ylmethyl)-5,9b-dihydro-1H-2a,5-diazabenzo[a]cyclobuta[c]cycloheptene-2,4-dione[ No CAS ]
5-(4-chloro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(3-bromo-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(3-fluoro-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5-(3-phenyl-propyl)-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(4-bromo-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-fluoro-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
4-[1-(4,6-dimethyl-pyrimidin-2-yloxy)-2,4-dioxo-9b-phenyl-1,3,4,9b-tetrahydro-2<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cyclohepten-5-yl]-butyric acid[ No CAS ]
5-(3-chloro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-methoxy-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
(4,6-dimethyl-pyrimidin-2-yloxy)-{1-[2-(2-methoxy-ethoxy)-ethyl]-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl}-acetic acid[ No CAS ]
(4,6-dimethyl-pyrimidin-2-yloxy)-[1-(3-methyl-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-acetic acid[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-methoxy-benzyl)-9b-<i>m</i>-tolyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-2-oxo-5-phenyl-1-(1H-tetrazol-5-ylmethyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
5-(4-<i>tert</i>-butyl-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
(4,6-dimethyl-pyrimidin-2-yloxy)-[1-(4-methyl-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-acetic acid[ No CAS ]
(4,6-dimethyl-pyrimidin-2-yloxy)-[1-(2-methyl-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-acetic acid[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-methoxy-benzyl)-9b-pentyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-methoxy-benzyl)-9b-<i>p</i>-tolyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
[1-(2-chloro-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-(4,6-dimethyl-pyrimidin-2-yloxy)-acetic acid[ No CAS ]
5-cyclohexylmethyl-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-[(5SR)-1-(3-chlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-(4,6-dimethylpyrimidin-2-yloxy)acetic acid[ No CAS ]
5-(2,6-dichloro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(2,5-difluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(2-morpholin-4-yl-ethyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(2,6-difluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
(4,6-dimethyl-pyrimidin-2-yloxy)-[1-(2-fluoro-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-acetic acid[ No CAS ]
(4,6-dimethyl-pyrimidin-2-yloxy)-[1-(3-fluoro-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-acetic acid[ No CAS ]
5-(2-cyclohexyl-ethyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-1-(4-methoxybenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-(2-fluoro-phenyl)-5-(4-methoxy-benzyl)-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-(3-fluoro-phenyl)-5-(4-methoxy-benzyl)-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
[1-(4-bromo-benzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5-yl]-(4,6-dimethyl-pyrimidin-2-yloxy)-acetic acid[ No CAS ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(4-methoxy-benzyl)-9b-(3-methoxy-phenyl)-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(2,4-difluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-[(5SR)-1-(4-chlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-(4,6-dimethylpyrimidin-2-yloxy)acetic acid[ No CAS ]
rac-(1SR,9bSR)-1-(4,6-dimethylpyrimidin-2-yloxy)-5-(4-methoxybenzyl)-9b-phenyl-5,9b-dihydro-1H-2a,5-diazabenzo[a]cyclobuta[c]cycloheptene-2,4-dione[ No CAS ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-2-oxo-5-phenyl-1-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
5-(3,4-difluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(2-chloro-6-fluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
5-(2,3-difluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
4-[1-(4,6-dimethyl-pyrimidin-2-yloxy)-2,4-dioxo-9b-phenyl-1,3,4,9b-tetrahydro-2<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cyclohepten-5-ylmethyl]-benzoic acid[ No CAS ]
5-(3,5-difluoro-benzyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione[ No CAS ]
4-[1-(4,6-dimethyl-pyrimidin-2-yloxy)-2,4-dioxo-9b-phenyl-1,3,4,9b-tetrahydro-2<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cyclohepten-5-ylmethyl]-benzoic acid methyl ester[ No CAS ]