Alternatived Products of [ 5444-83-7 ]
Product Details of [ 5444-83-7 ]
CAS No. : 5444-83-7
MDL No. : MFCD22207693
Formula :
C9 H11 ClN4
Boiling Point :
-
Linear Structure Formula : -
InChI Key : FDRPGDDGRMEJSU-UHFFFAOYSA-N
M.W :
210.66
Pubchem ID : 227574
Synonyms :
Calculated chemistry of [ 5444-83-7 ]
Physicochemical Properties
Num. heavy atoms :
14
Num. arom. heavy atoms :
9
Fraction Csp3 :
0.44
Num. rotatable bonds :
3
Num. H-bond acceptors :
3.0
Num. H-bond donors :
0.0
Molar Refractivity :
56.02
TPSA :
43.6 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
Yes
P-gp substrate :
No
CYP1A2 inhibitor :
Yes
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
No
CYP2D6 inhibitor :
No
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-5.77 cm/s
Lipophilicity
Log Po/w (iLOGP) :
2.34
Log Po/w (XLOGP3) :
2.56
Log Po/w (WLOGP) :
2.28
Log Po/w (MLOGP) :
1.29
Log Po/w (SILICOS-IT) :
2.0
Consensus Log Po/w :
2.09
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-3.04
Solubility :
0.194 mg/ml ; 0.000919 mol/l
Class :
Soluble
Log S (Ali) :
-3.12
Solubility :
0.159 mg/ml ; 0.000753 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-3.56
Solubility :
0.0574 mg/ml ; 0.000272 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.85
Application In Synthesis of [ 5444-83-7 ]
* 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.
Downstream synthetic route of [ 5444-83-7 ]
1
[ 5444-83-7 ]
[ 17356-08-0 ]
[ 6165-01-1 ]
Yield Reaction Conditions Operation in experiment
With propan-1-ol
2
[ 5444-83-7 ]
[ 6943-34-6 ]
Yield Reaction Conditions Operation in experiment
With palladium on activated charcoal; ethanol; magnesium oxide Hydrogenation;
3
[ 5444-83-7 ]
[ 2715-70-0 ]
Yield Reaction Conditions Operation in experiment
With ethanol; ammonia
4
[ 41259-67-0 ]
[ 122-51-0 ]
[ 5444-83-7 ]
Yield Reaction Conditions Operation in experiment
With ethanesulfonic acid for 68h; Ambient temperature;
Reference:
[1]Kelley, James L.; Morris Bullock; Krochmal, Mark P.; McLean, Ed W.; Linn, James A.; Durcan, Micheal J.; Cooper, Barrett R.
[Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3207 - 3216]
5
[ 5444-83-7 ]
[ 124-40-3 ]
(9-Butyl-9H-purin-6-yl)-dimethyl-amine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
59%
In ethanol for 18h; Ambient temperature;
Reference:
[1]Kelley, James L.; Morris Bullock; Krochmal, Mark P.; McLean, Ed W.; Linn, James A.; Durcan, Micheal J.; Cooper, Barrett R.
[Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3207 - 3216]
6
[ 5444-83-7 ]
[ 765-30-0 ]
(9-Butyl-9H-purin-6-yl)-cyclopropyl-amine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
86%
With triethylamine In ethanol for 72h; Ambient temperature;
Reference:
[1]Kelley, James L.; Morris Bullock; Krochmal, Mark P.; McLean, Ed W.; Linn, James A.; Durcan, Micheal J.; Cooper, Barrett R.
[Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3207 - 3216]
Yield Reaction Conditions Operation in experiment
/BRN= 150825/;
8
[ 87-42-3 ]
[ 71-36-3 ]
[ 5444-83-7 ]
Yield Reaction Conditions Operation in experiment
89%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 70℃; for 12h;
9
[ 5444-83-7 ]
[ 141-97-9 ]
[ 1142812-38-1 ]
Yield Reaction Conditions Operation in experiment
89%
With caesium carbonate In dimethyl sulfoxide at 60℃; for 2h;
Reference:
[1]Location in patent: body text
Quy, Gui-Rong; Mao, Zhi-Jie; Niuy, Hong-Ying; Wang, Dong-Chao; Xia, Chao; Guo, Hai-Ming
[Organic Letters, 2009, vol. 11, # 8, p. 1745 - 1748]
10
[ 5444-83-7 ]
[ 141-97-9 ]
[ 1142812-46-1 ]
Yield Reaction Conditions Operation in experiment
71%
With potassium carbonate In dimethyl sulfoxide at 80℃; for 7h;
Reference:
[1]Location in patent: body text
Quy, Gui-Rong; Mao, Zhi-Jie; Niuy, Hong-Ying; Wang, Dong-Chao; Xia, Chao; Guo, Hai-Ming
[Organic Letters, 2009, vol. 11, # 8, p. 1745 - 1748]
11
[ 5444-83-7 ]
[ 141-97-9 ]
[ 1142812-51-8 ]
Yield Reaction Conditions Operation in experiment
95%
With potassium carbonate In dimethyl sulfoxide at 20 - 80℃; Microwave irradiation;
65%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 8h;
Reference:
[1]Location in patent: experimental part
Guo, Hai-Ming; Mao, Zhi-Jie; Niu, Hong-Ying; Wang, Dong-Chao; Zhang, Gui-Sheng; Qu, Gui-Rong
[ARKIVOC, 2010, vol. 2010, # 9, p. 300 - 307]
[2]Location in patent: body text
Quy, Gui-Rong; Mao, Zhi-Jie; Niuy, Hong-Ying; Wang, Dong-Chao; Xia, Chao; Guo, Hai-Ming
[Organic Letters, 2009, vol. 11, # 8, p. 1745 - 1748]
12
[ 5444-83-7 ]
[ 111-42-2 ]
[ 1181816-23-8 ]
Yield Reaction Conditions Operation in experiment
75%
In water at 100℃; for 0.166667h; Microwave irradiation;
13
[ 5444-83-7 ]
[ 123-54-6 ]
[ 1142812-51-8 ]
Yield Reaction Conditions Operation in experiment
76%
With potassium carbonate In dimethyl sulfoxide at 80℃; for 0.166667h; Microwave irradiation;
Reference:
[1]Guo, Hai-Ming; Zhang, Yu; Niu, Hong-Ying; Wang, Dong-Chao; Chu, Zhi-Liang; Qu, Gui-Rong
[Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2065 - 2068]
14
[ 5444-83-7 ]
[ 57625-28-2 ]
[ 62673-31-8 ]
[ 1510826-43-3 ]
Yield Reaction Conditions Operation in experiment
72%
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20 - 70℃; Inert atmosphere; regioselective reaction;
Reference:
[1]Wang, Dong-Chao; Niu, Hong-Ying; Xie, Ming-Sheng; Qu, Gui-Rong; Wang, Hui-Xuan; Guo, Hai-Ming
[Organic Letters, 2014, vol. 16, # 1, p. 262 - 265]
15
[ 5444-83-7 ]
7-butyl-7H-[1,2,4]triazolo[4,3-g]purine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrazine hydrate / methanol / 1 h / Reflux
2: 12 h / Reflux
16
[ 5444-83-7 ]
C9 H14 N6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With hydrazine hydrate In methanol for 1h; Reflux;
17
[ 109-65-9 ]
[ 87-42-3 ]
[ 5444-83-7 ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
18
[ 5444-83-7 ]
[ 98-80-6 ]
[ 1284287-32-6 ]
Yield Reaction Conditions Operation in experiment
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In toluene at 100℃; Inert atmosphere; Schlenk technique; Sealed tube;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 100℃; for 18h;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 100℃; for 18h; Inert atmosphere;
Reference:
[1]Gou, Quan; Li, Wenxi; Zhao, Qingsheng; Xie, Jia; Luo, Ping; Cao, Guang; Chen, Suiyun; Qin, Jun
[European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4089 - 4094]
[2]Yang, Qi-Liang; Liu, Ying; Liang, Lei; Li, Zhi-Hao; Qu, Gui-Rong; Guo, Hai-Ming
[Journal of Organic Chemistry, 2022, vol. 87, # 9, p. 6161 - 6178]
[3]Yang, Qi-Liang; Liu, Ying; Luo, Yi-Rui; Li, Zhi-Hao; Jia, Hong-Wei; Fu, Ya-Bo; Qu, Gui-Rong; Guo, Hai-Ming
[Organic Letters, 2022, vol. 24, # 23, p. 4234 - 4239]
19
[ 5444-83-7 ]
[ 98-80-6 ]
9-butyl-6-(2-nitrophenyl)-9H-purine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) ; potassium carbonate / toluene / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube
2: tert.-butylnitrite; palladium diacetate; oxygen / 110 °C / 760.05 Torr / Schlenk technique; Sealed tube
Reference:
[1]Gou, Quan; Li, Wenxi; Zhao, Qingsheng; Xie, Jia; Luo, Ping; Cao, Guang; Chen, Suiyun; Qin, Jun
[European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4089 - 4094]
20
[ 5444-83-7 ]
[ 98-80-6 ]
9-butyl-6-(o-tolyl)-9H-purine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: tetrakis-(triphenylphosphine)-palladium; potassium carbonate / toluene; water monomer; ethanol / 18 h / 100 °C
2: [RhCp*(OAc)2 ] / methanol / 17 h / 50 °C / Electrolysis; Green chemistry
Reference:
[1]Yang, Qi-Liang; Liu, Ying; Liang, Lei; Li, Zhi-Hao; Qu, Gui-Rong; Guo, Hai-Ming
[Journal of Organic Chemistry, 2022, vol. 87, # 9, p. 6161 - 6178]