Chemistry Reference
In-Depth Information
Typical procedure. 6-Chlorocarbonylamino-1,4,5,6-tetrahydro-5-imino-3-methyl-1,4-diphe-
nylpyrazolo[4
0
,3
0
:5,6]pyrano[2,3-d]pyrimidine 149 [97]:
To a solution of 6-amino-
1,4,5,6-tetrahydro-5-imino-3-methyl-1,4-diphenylpyrazolo[4
0
,3
0
:5,6]pyrano[2,3-d]py-
rimidine (0.37 g, 0.001 mol) in dry benzene (100 mL) was added an excess of ethyl
chloroformate (0.5 mL) and the mixture was refluxed for 10 h. After cooling, the
solid product formed was collected and crystallized from benzene/EtOH (3:1) to
furnish white flakes; yield 0.35 g (81%).
Desmethylsetraline 150 has been transformed into the corresponding carbamoyl
chloride 151 by ethyl chloroformate in acetonitrile [98].
O
NH
2
HN
Cl
EtOCOCl
MeCN, K
2
CO
3
, 2h
Cl
Cl
Cl
Cl
150
151
Various carbamoyl chlorides 153, 155, and 157 of ortho-dimethylamino-substituted
anilines 152 and 156 or 6-dimethylamino-5-aminopyrimidine 154 have been pre-
pared with phenyl chloroformate [99].
Me
Me
Me
Me
N
N
H
N
Cl
NH
2
PhOCOCl
O
pyridine
O
O
Me
Me
152
153
Me
Me
Me
Me
N
N
H
N
NH
2
l
N
PhOCOCl
N
O
pyridine
N
O
N
O
Me
Me
154
155
Me
Me
Me
Me
N
N
H
N
l
NH
2
PhOCOCl
O
pyridine
O
Me
O
Me
Me
Me
156
157
