* 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.
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
2
[ 22325-27-5 ]
[ 35144-22-0 ]
Reference:
[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2776 - 2795
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
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 ]
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 ]
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 ]
(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 ]
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-(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-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 ]
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-(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 ]
[1-(3-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 ]
(4,6-dimethyl-pyrimidin-2-yloxy)-[2-oxo-5-phenyl-1-(3-phenyl-propyl)-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)-9b-phenyl-5-(4-trifluoromethyl-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-cyclohexylmethyl-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 ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-1-(4-methoxybenzyl)-2-oxo-5-m-tolyl-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-phenyl-5-(2,4,6-trimethyl-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-phenyl-5-(2-trifluoromethyl-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 ]
rac-(S)-(4,6-dimethylpyrimidin-2-yloxy)-[(5S)-1-(4-methoxybenzyl)-2-oxo-5-p-tolyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
[1-(4-<i>tert</i>-butyl-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)-9b-phenyl-5-(3-trifluoromethyl-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 ]
5-biphenyl-4-ylmethyl-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-(4-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 ]
1-(4,6-dimethyl-pyrimidin-2-yloxy)-9b-phenyl-5-(2,3,4-trifluoro-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-phenyl-5-(2-trifluoromethoxy-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 ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-1-(2-morpholin-4-ylethyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
[1-(2-cyclohexyl-ethyl)-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 ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-5-(3-chlorophenyl)-1-(4-methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]
[1-(3,5-difluoro-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)-9b-phenyl-5-(3,4,5-trifluoro-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-(2,6-difluoro-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 ]
rac-(SR)-[(5SR)-1-(2,6-dichlorobenzyl)-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-4-{(5SR)-5-[(SR)-carboxy-(4,6-dimethylpyrimidin-2-yloxy)methyl]-2-oxo-5-phenyl-2,3,4,5-tetrahydrobenzo[e][1,4]diazepin-1-ylmethyl}benzoic acid methyl ester[ No CAS ]
rac-(SR)-[(5SR)-1-(2-chloro-6-fluorobenzyl)-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)-9b-phenyl-5-(2,4,5-trifluoro-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-(2,3-difluoro-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 ]
rac-(SR)-(4,6-dimethylpyrimidin-2-yloxy)-[(5SR)-2-oxo-5-phenyl-1-(2,4-difluorobenzyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid[ No CAS ]