[ CAS No. 5878-61-5 ]

Name: 5878-61-5|7-(2-Chloroethyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione|98%
Brand: Ambeed
SKU: A450562
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Quality Control of [ 5878-61-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 5878-61-5 ]

CAS No. :	5878-61-5	MDL No. :	MFCD00005760
Formula :	C₉H₁₁ClN₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	242.66 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 5878-61-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.44
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.64
TPSA :	61.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	0.07
Log Po/w (WLOGP) :	-0.33
Log Po/w (MLOGP) :	0.03
Log Po/w (SILICOS-IT) :	0.35
Consensus Log Po/w :	0.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	5.15 mg/ml ; 0.0212 mol/l
Class :	Very soluble
Log S (Ali) :	-0.92
Solubility :	29.0 mg/ml ; 0.12 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.71
Solubility :	4.72 mg/ml ; 0.0195 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.31

Safety of [ 5878-61-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312+P330-P501	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5878-61-5 ]

* 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 [ 5878-61-5 ]

[ 5878-61-5 ] Synthesis Path-Downstream 1~34

1
[ 107-10-8 ]
[ 5878-61-5 ]
[ 1221-11-0 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

2
[ 5878-61-5 ]
[ 108-91-8 ]
[ 3842-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

3
[ 5878-61-5 ]
[ 75-04-7 ]
[ 95390-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

4
[ 5878-61-5 ]
[ 75-31-0 ]
[ 94523-41-8 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

5
[ 5878-61-5 ]
[ 74-89-5 ]
[ 70919-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

6
[ 5878-61-5 ]
[ 100-46-9 ]
[ 22680-61-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

7
[ 5878-61-5 ]
[ 22247-84-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium diethylmalonate
	Multi-step reaction with 2 steps 1: H₂O; KI 2: sodium compound of malonic acid diethyl ester; ethanol

Reference： [1]Cacace et al. [Annali di Chimica, 1956, vol. 46, p. 99,102,104]
[2]Cacace et al. [Annali di Chimica, 1956, vol. 46, p. 99,102,104]

8
[ 5878-61-5 ]
[ 65919-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	With water; potassium iodide

Reference： [1]Cacace et al. [Annali di Chimica, 1956, vol. 46, p. 99,102,104]

9
[ 5878-61-5 ]
[ 35206-02-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; ammonia

Reference： [1]Current Patent Assignee: CHEMIEWERK HOMBURG - DE1011424, 1954, B

10
[ 519-37-9 ]
[ 5878-61-5 ]

Reference： [1]Annali di Chimica,1956,vol. 46,p. 99,102,104

11
[ 58-55-9 ]
[ 107-06-2 ]
[ 5878-61-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide for 4h; Heating;
90%	With sodium hydroxide In water; isopropyl alcohol at 78 - 80℃; for 76.5h; Heating;
	In water; dimethyl sulfoxide	103 EXAMPLE 103 EXAMPLE 103 After 400 mg (60%, 10 mmol) of sodium hydride had been washed, under argon atmosphere, with dry hexane, it was dissolved in 5 ml of dimethyl sulfoxide. The mixture was stirred at 70°-75° C. for 30 minutes, and then it was cooled to room temperature. To the mixture was added a suspension of 1.8 g (10 mmol) of theophylline in 5 ml of dimethyl sulfoxide, and the whole mixture was stirred for 30 minutes. Further, a solution of 20 g (200 mmol) of 1,2-dichloroethane in 10 ml of dimethyl sulfoxide was added dropwise to the mixture over 15 minutes. The mixture was stirred at room temperature for a further 16 hours, after which water was added, and then the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with chloroform-methanol (100:1), to give 1.62 g (6.68 mmol) of 7-(2-chloroethyl)theophylline.

Reference： [1]Kalcheva, Veneta B.; Apostolova, Tatiana M.; Anakieva, Violeta Z. [Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 1, p. 165 - 168]
[2]Peikov; Zlatkov; Markov; Danchev; Ivanov; Panova [European Journal of Medicinal Chemistry, 1994, vol. 29, # 4, p. 295 - 299]
[3]Current Patent Assignee: TERUMO CORPORATION - US4673684, 1987, A

12
[ 100-60-7 ]
[ 5878-61-5 ]
7-<2-(N-methyl-N-cyclohexyl)-aminoethyl>-1,3-dimethylxanthine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; for 4.75h;

Reference： [1]Peikov; Zlatkov; Markov; Danchev; Ivanov; Panova [European Journal of Medicinal Chemistry, 1994, vol. 29, # 4, p. 295 - 299]

13
[ 56346-57-7 ]
[ 5878-61-5 ]
7-[2-[4-(p-fluorobenzoyl)-piperidino]-ethyl]-theophylline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.5 g	at 100℃; for 1h;

Reference： [1]Thiele; Jahn; Geissmann; Zirngibl [Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 1, p. 1 - 4]

14
[ 1518-86-1 ]
[ 5878-61-5 ]
[ 62401-66-5 ]

Yield	Reaction Conditions	Operation in experiment
62%

Reference： [1]Rucker; Neugebauer; Heiden [Arzneimittel-Forschung/Drug Research, 1988, vol. 38, # 4, p. 497 - 501]

15
[ 5878-61-5 ]
[ 72996-78-2 ]
[ 131729-08-3 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium carbonate; sodium iodide In acetonitrile Heating;

Reference： [1]Bagley; Thomas; Rudo; Spencer; Doorley; Ossipov; Jerussi; Benvenga; Spaulding [Journal of Medicinal Chemistry, 1991, vol. 34, # 2, p. 827 - 841]

16
[ 5878-61-5 ]
[ 40172-95-0 ]
7-<3-<4-(2-Furoyl)-1-piperazinyl>-ethyl>-theophyllin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; for 3h;

Reference： [1]Thiele; Jahn; Geissmann; Zirngibl [Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 1, p. 1 - 4]

17
[ 5878-61-5 ]
[ 145276-53-5 ]
6-<4-<2-(7-theophyllin)-ethyl>-1-piperazinyl>-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium carbonate In i-Amyl alcohol Heating;

Reference： [1]Corsano; Scapicchi; Strappaghetti [Archiv der Pharmazie, 1994, vol. 327, # 10, p. 631 - 635]

18
[ 5878-61-5 ]
[ 159430-52-1 ]
5-<4-<2-(7-theophyllin)-ethyl>-1-piperazinyl>-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium carbonate In i-Amyl alcohol for 20h; Heating;

Reference： [1]Corsano; Scapicchi; Strappaghetti [Archiv der Pharmazie, 1994, vol. 327, # 10, p. 631 - 635]

19
[ 5878-61-5 ]
2-methyl-5-(1-piperazinyl)-3(2H)-pyridazinone [ No CAS ]
2-methyl-5-<4-<2-(7-theophyllin)-ethyl>-1-piperazinyl>-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With sodium carbonate In i-Amyl alcohol for 20h; Heating;

Reference： [1]Corsano; Scapicchi; Strappaghetti [Archiv der Pharmazie, 1994, vol. 327, # 10, p. 631 - 635]

Yield	Reaction Conditions	Operation in experiment
	Rk. mit Nicotinamid --> NATH;

Yield	Reaction Conditions	Operation in experiment
	7-(2-Hydroxy-aethyl)-theophyllin, Thionylchlorid, wfr. CHCl3, 60grad, 8 Std.;
	Theophyllin, α-Br-β-Cl-propan;
	7-(ss-Hydroxyethyl)-theophyllin, Thionylchlorid;

	7β-Hydroxyethyltheophyllin, SOCl2;
		The following xanthines may be mentioned as examples of the xanthines of formula I mentioned above, used according to said particular embodiment: ... 1,3-dimethyl-7-hydroxymethylxanthine, 1,3-dimethyl-7-(morpholinomethyl)xanthine, 1,3,7-triethylxanthine, 3,7-diethyl-1-(prop-2-ynyl)xanthine and 7-(2-chloroethyl)-1,3-dimethylxanthine.
		The method of claim 1 wherein the xanthine of formula (I) is selected from the group consisting of: ... 1,3-dimethyl-7-hydroxymethylxanthine, 1,3-dimethyl-7-(morpholinomethyl)xanthine, 1,3,7-triethylxanthine, 3,7-diethyl-1-(2-propynyl)xanthine and 7-(2-chloroethyl)-1,3-dimethylxanthine.

22
[ 5878-61-5 ]
[ 109018-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - DE1014998, 1954, B

23
[ 5878-61-5 ]
[ 32898-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - DE1014998, 1954, B

24
[ 5878-61-5 ]
[ 59496-07-0 ]
[ 263543-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In methanol; butanone	B.2 EXAMPLE B2 EXAMPLE B2 A mixture of 1,2,3,4-tetrahydro-[1]benzothieno[2,3-c]pyridine hydrochloride (1:1) (0.00057 mol), 7-(2-chloroethyl)-1,3-dimethyl-7H-purine-2,6-(1H,3H)-dione (0.100 g) and Na2CO3 (0.100 g) in 2-butanone (2 ml) was stirred over the weekend at 100° C. The desired compound was isolated and purified by high-performance liquid chromato-graphy over Kromasil Spherical underivated silica gel (55 g, 60 Å, 5 μm) (column: 2 cm I.D.; eluent: CH2Cl2/(CH2Cl2/CH3OH 90/10)/CH3OH (0 minutes) 100/0/0, (10.50 minutes) 0/100/0, (12.50 minutes) 50/0/50, (14.00 minutes) 0/0/100, (15.01-20.00 minutes) 100/0/0). The pure fractions were collected and the solvent was evaporated, yielding 0.070 g of 7-[2-(3,4-dihydrobenzothieno[2,3-c]pyridin-2(1H)-yl)ethyl]-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (compound 7).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US6495555, 2002, B1

25
[ 5878-61-5 ]
[ 40172-95-0 ]
7-[3-[4-(2-furoyl)-1-piperazinyl]-2-hydroxypropyl]-theophylline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In dichloromethane	5 7-[3-[4-(2-furoyl)-1-piperazinyl]-2-hydroxypropyl]-theophylline (Sgd 269-76) STR10 EXAMPLE 5 7-[3-[4-(2-furoyl)-1-piperazinyl]-2-hydroxypropyl]-theophylline (Sgd 269-76) STR10 A mixture of 2 g (8.26 mMol) 7-(2-chloro-ethyl)-theophylline and 3.78 g (21 mMol) N-furoyl piperazine is melted at 100° C. upon an oil bath and held for 3 hours at that temperature. After cooling, the solidified mass is dissolved in methylene chloride. The solution is extracted with water and subsequently shaken twice with 10% hydrochloric acid. The combined aqueous phases are made alkaline with sodium hydroxide solution and again extracted with methylene chloride and the resulting extract is dried over MgSO4 and concentrated. The residue is washed twice with water at 60° C. and again dissolved in methylene chloride. The solution is dried over MgSO4, relieved of solvent by evaporation, and recrystallized in ethyl acetate, yielding the pure product having a melting point of 142°-144° C. C18 H22 N6 O4: 386.41: calc. C 55.95; H 5.74; N 21.75; fd. C 55.86; H 5.84; N 21.71

Reference： [1]Current Patent Assignee: SIEGFRIED CH 4800 ZOFINGEN - US4603204, 1986, A

26
fluorobenzoylpiperidine hydrochloride [ No CAS ]
[ 56346-57-7 ]
[ 5878-61-5 ]
7-[2-[4-(p-fluorobenzoyl)-piperidino]-ethyl]-theophylline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide In tetrachloromethane; ethyl acetate	1 (Sgd 195-78) STR5 EXAMPLE 1 7-[2-[4-(p-fluorobenzoyl)-piperidino]-ethyl]-theophylline (Sgd 195-78) STR5 25.6 g (0.124M) 4-(p-fluorobenzoyl)-piperidine is heated together with 15.0 g (0.062M) 7-(2-chloroethyl)-theophylline in the solid state in a round flask to 100° C. during one hour. It is cooled down to 60° C. and ethyl acetate is added while stirring until a homogeneous suspension is present. After cooling and filtering off of the separated fluorobenzoylpiperidine hydrochloride, 2n hydrochloric acid is added to the filtrate for the precipitation of the raw product. The residue, separated by filtration, is washed twice, each time with water and ethyl acetate, and subsequently a layer of ethyl acetate is added and 100 ml sodium hydroxide solution is added. After agitation and separation of the phases, the principal amount of the product resides in the organic phase; in order to obtain additional amounts of product, the aqueous phase is shaken twice, each with 100 ml ethyl acetate. The combined organic phases are washed with saturated NaCl solution, treated with activated carbon, dried over MgSO4 and filtered. After distilling off of the solvent, the filtrate yields 20.4 g (80%) raw crystalline product. For additional purification, the residue is suspended in 250 ml carbon tetrachloride and heated at reflux temperature. The dark brown solution obtained thereby, becomes light orange after treatment with activated carbon and on cooling yields 14.5 g white product with an mp of 143°-145° C., which is shown to be pure by thin layer chromatography. A pure product of identical composition according to thin layer chromatography which melts under decomposition at 248° C. was obtained by heating the starting materials mixed at the same ratio to 120° C. for five hours, subsequently boiling 7 hours in n-propanol, corresponding working-up and crystallizing from carbon tetrachloride.

Reference： [1]Current Patent Assignee: SIEGFRIED CH 4800 ZOFINGEN - US4668786, 1987, A

27
3-(3,6-dihydro-1(2H)-pyridinyl)-1H-indole [ No CAS ]
[ 67-66-3 ]
[ 5878-61-5 ]
[ 108-88-3 ]
3,7-dihydro-7-[2-[3,6-dihydro-4-(1H-indol-3-yl)-1(2H)-pyridinyl]ethyl]-1,3-dimethyl-1H-purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.1 parts (51.6%)	With potassium iodide; sodium carbonate In methanol	6 EXAMPLE 6 EXAMPLE 6 A mixture of 3.8 parts of 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione, 3 parts of 3-(3,6-dihydro-1(2H)-pyridinyl)-1H-indole, 8 parts of sodium carbonate, 0.1 parts of potassium iodide and 270 parts of methylbenzene was stirred and refluxed for 20 hours. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried in vacuo at 120° C., yielding 3.1 parts (51.6%) of 3,7-dihydro-7-[2-[3,6-dihydro-4-(1H-indol-3-yl)-1(2H)-pyridinyl]ethyl]-1,3-dimethyl-1H-purine-2,6-dione; mp. 196.5° C. (compound 21).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US4548939, 1985, A

28
[ 67-66-3 ]
[ 5878-61-5 ]
[ 108-10-1 ]
[ 17403-09-7 ]
7-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4 parts (50%)	With potassium iodide; sodium carbonate In methanol; water	1 EXAMPLE 1 EXAMPLE 1 A mixture of 5 parts of 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione, 4 parts of 3-(4-piperidinyl)-1H-indole, 8 parts of sodium carbonate, 1 part of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred and refluxed overnight. The reaction mixture was cooled, water was added and the layers were separated. The organic phase was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone, yielding 4 parts (50%) of 7-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione; mp. 201.2° C. (compound 1).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US4548939, 1985, A

29
[ 5878-61-5 ]
[ 108-10-1 ]
[ 62555-50-4 ]
[ 102144-79-6 ]

Yield	Reaction Conditions	Operation in experiment
2.5 parts (43%)	With potassium iodide; sodium carbonate In methanol; chloroform	2 EXAMPLE 2 EXAMPLE 2 A mixture of 3.65 parts of 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione, 3 parts of 3-(4-piperidinyl)-1H-indol-5-ol, 4.25 parts of sodium carbonate, 0.1 parts and potassium iodide and 200 parts of 4-methyl-2-pentanone was stirred and refluxed overnight. The whole was filtered while hot and the filtrate was evaporated. The residue was suspended in 45 parts of trichloromethane and 2.4 parts of methanol. The product was filtered off, washed with 16 parts of methanol and dried, yielding 2.5 parts (43%) of 3,7-dihydro-7-[2-[4-(5-hydroxy-1H-indol-3-yl)-1-piperidinyl]ethyl]-1,3-dimethyl-1H-purine-2,6-dione; mp. 232.5° C. (compound 2).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US4548939, 1985, A

30
[ 39512-50-0 ]
[ 5878-61-5 ]
KMUP-1 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water Alkaline conditions; Reflux; Cooling;	1 Embodiment 1Synthesis of PulmodilThe first preferred embodiment of the present invention is Pulmodul. Method 1: 2-Chloroethyl theophylline, 2-chlorophenyl piperazine and sodium hydroxide (NaOH) (or sodium hydrogen carbonate (NaHCO3)) were dissolved in hydrous ethanol solution based on the molecular weight percentage and heated under reflux for three hours. After overnight cooling, the supernatant was decanted for proceeding the vacuum concentration and dry process, and then one-fold volume of ethanol and three-fold volume of 2N hydrochloric acid (HCl) were added therein to dissolve at 50° C. to 60° C. as a saturated solution with pH 1.2. The saturated solution was sequentially decolorized with activated charcoal, filtered, deposited overnight and filtered to obtain Pulmodil with a white crystal. Pulmodil had a chemical formula as 7-[2-[4-(2-chlorobenzene)piperazinyl]ethyl]-1,3-dimethylxanthine.HCl, which had a melting point of 249° C. to 252° C. The reaction formula was illustrated as follows. Further, the purity of Pulmodil was determined with high performance liquid chromatography (HPLC).
	With sodium carbonate In tetrahydrofuran for 2h; Reflux;	1 Embodiment 1: Synthesis of KMUP-1Twenty grams of 7-ethylchloro-theophylline is added into a flask containing 50 ml of tetrahydrofuran (THF) and 60 ml of 1-(2-chlorophenyl)-piperazine, and a suitable amount of sodium carbonate (Na2CO3) is added therein. The flask is connected with a condensing tube, and the reaction mixture in the flask is heated to boil to reflux for 2 hours. The reaction mixture is cooled after the reaction is completed, the product is dissolved and eluted with ethanol, and the elutant is collected, concentrated and heated under the water bath. The elutant is filtered while heated, and the filtered solution is cooled and the white crystal product is obtained. The white crystal product is 7-[2-[4-(2-chlorobenzene)piperazinyl]ethyl]-1,3-dimethylxanthine (abbreviated as KMUP-1). The reaction formula is illustrated as follows. In addition, tetrahydrofuran can be substituted for methanol or ethanol.

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - US2010/280040, 2010, A1 Location in patent: Page/Page column 2-3
[2]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - US2011/118464, 2011, A1 Location in patent: Page/Page column 4

31
[ 5878-61-5 ]
[ 407-25-0 ]
1,3-dimethyl-8-(trifluoromethyl)-7-(2-chloroethyl)-3,7-dihydro-1H-purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With pyridine N-oxide; ruthenium tris(4,4'-bis(dinonylmethyl)-2,2'-bipyridine) In dichloromethane; acetonitrile at 20℃; for 24h; Irradiation;	4.3.1. Procedure for the visible light-catalyzed reaction General procedure: A flame-dried reaction vessel with a magnetic stirring bar was sequentially charged with coumarin or p-dimethoxybenzene or 7-(2-Chloroethyl)theophylline (0.4mmol), PC (0.004mmol), pyridine N-oxide (0.82mmol, 78mg), CH2Cl2 (0.5mL) and CH3CN (0.5mL). Trifluoroacetic anhydride (0.8mmol, 168mg) was then added to the resulting homogeneous solution. The mixture was stirred at room temperature under irradiation from a blue LED. The solvent in the reaction mixture was removed under reduced pressure. The residue was redissolved in 2mL of CH3CN, and extracted 5 times with hexane (5mL each time). The PC was extracted into the hexane layer and separated for use in the next reaction. The CH3CN layer was dried with Na2SO4 and concentrated under vacuum. After separation and evaporation, the residue was purified by column chromatography on silica gel (200-300 mesh size) using petroleum ether/EtOAc as the eluent to give the trifluoromethyl coumarin.

Reference： [1]Zhang, Xiaodan; Li, Yaming; Hao, Xinyu; Jin, Kun; Zhang, Rong; Duan, Chunying [Tetrahedron, 2018, vol. 74, # 15, p. 1742 - 1748]

32
[ 5878-61-5 ]
1-[2-(6-amino-9H-purin-9-yl)ethyl]-5-methyl-2,3-dihydro-1H-indole-2,3-dione [ No CAS ]
1,3-dimethyl-7-[2-(5-methyl-2,3-dihydro-1Hindol-1-yl)ethyl]-1H-purine-2,6(3H,7H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 1-[2-(6-amino-9H-purin-9-yl)ethyl]-5-methyl-2,3-dihydro-1H-indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 10 - 25℃; for 0.5h; Stage #2: 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione In N,N-dimethyl-formamide; mineral oil at 60℃; for 3h;	Isatin derivatives 1a-1c, 2a, and 2b (generalprocedure). General procedure: Isatin, 5-methylisatin, or 5-ethylisatin(10 mmol) was dissolved in 20 mL of DMF, and 0.42 gof sodium hydride (10 mmol, 60% suspension inmineral oil) was added with stirring on a magneticstirred at 10°C. The mixture was allowed to warm upto 25°C over a period of 30 min, and 7-(2-chloroethyl)-theophylline (2.43 g, 10 mmol) or 9-(2-bromoethyl)-adenine (2.42 g, 10 mmol) was added. The resultingsolution was stirred at 60°C for 3 h and poured intoa mixture of 100 g of ice and 50 mL of water. Themixture spontaneously warmed up to 25°C, and thesolid product was filtered off, washed with diethylether, and dried under reduced pressure (18 mm Hg,water-jet pump).

Reference： [1]Abzalilov, T. A.; Bogdanov, A. V.; Mironov, V. F.; Samorodov, A. V.; Sirazieva, A. R.; Voloshina, A. D. [Russian Journal of Organic Chemistry, 2022, vol. 58, # 3, p. 327 - 334][Zh. Org. Khim., 2022, vol. 58, # 3, p. 317 - 325]

33
[ 5878-61-5 ]
1-[2-(6-amino-9H-purin-9-yl)ethyl]-2,3-dihydro-1H-indole-2,3-dione [ No CAS ]
7-[2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)ethyl]-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 1-[2-(6-amino-9H-purin-9-yl)ethyl]-2,3-dihydro-1H-indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 10 - 25℃; for 0.5h; Stage #2: 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione In N,N-dimethyl-formamide; mineral oil at 60℃; for 3h;	Isatin derivatives 1a-1c, 2a, and 2b (generalprocedure). General procedure: Isatin, 5-methylisatin, or 5-ethylisatin(10 mmol) was dissolved in 20 mL of DMF, and 0.42 gof sodium hydride (10 mmol, 60% suspension inmineral oil) was added with stirring on a magneticstirred at 10°C. The mixture was allowed to warm upto 25°C over a period of 30 min, and 7-(2-chloroethyl)-theophylline (2.43 g, 10 mmol) or 9-(2-bromoethyl)-adenine (2.42 g, 10 mmol) was added. The resultingsolution was stirred at 60°C for 3 h and poured intoa mixture of 100 g of ice and 50 mL of water. Themixture spontaneously warmed up to 25°C, and thesolid product was filtered off, washed with diethylether, and dried under reduced pressure (18 mm Hg,water-jet pump).

34
[ 5878-61-5 ]
[ 76-04-0 ]
8-(chlorodifluoromethyl)-7-(2-chloroethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With 1,2,3-trimethoxybenzene; (3,5-bis(trifluoromethyl)phenyl)-λ³-iodanediyl diacetate In chloroform-d1 at 20℃; for 18h; Sealed tube; Irradiation; Inert atmosphere;

Reference： [1]Lin, Daniel; Krishnamurti, Vinayak; Prakash, G. K. Surya [European Journal of Organic Chemistry, 2022]

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[ CAS No. 5878-61-5 ]

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[ 5878-61-5 ] Synthesis Path-Downstream 1~34

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