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[ CAS No. 1211522-68-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1211522-68-7
Chemical Structure| 1211522-68-7
Chemical Structure| 1211522-68-7
Structure of 1211522-68-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1211522-68-7 ]

CAS No. :1211522-68-7 MDL No. :MFCD16249844
Formula : C6H4Cl2N4 Boiling Point : -
Linear Structure Formula :- InChI Key :WAVYWHRLGFPXMJ-UHFFFAOYSA-N
M.W : 203.03 Pubchem ID :52987827
Synonyms :

Calculated chemistry of [ 1211522-68-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.67
TPSA : 54.46 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) : 1.46
Log Po/w (XLOGP3) : 2.49
Log Po/w (WLOGP) : 1.97
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 2.8
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.122 mg/ml ; 0.000599 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.107 mg/ml ; 0.000526 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.0329 mg/ml ; 0.000162 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 1211522-68-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1211522-68-7 ]

* 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 [ 1211522-68-7 ]

[ 1211522-68-7 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 110-87-2 ]
  • [ 1211522-68-7 ]
  • [ 1346447-97-9 ]
YieldReaction ConditionsOperation in experiment
54% With toluene-4-sulfonic acid; In ethyl acetate; at 50.0℃; for 12.0h; 4,6-Dichloro-3-methyl-1H-pyrazolo [3,4-d] pyrimidine(70 mg, 0.34 mmol) was added to ethyl acetate (2 mL), and dihydropyran (0.2 mL, 2.3 mmol) and p-toluenesulfonic acid (3 mg) were added. The mixture was stirred at 50 C for 12 hours. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate and water, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was subjected to column chromatography to obtain the target compound. (30 mg, 54%).
Example 12: Synthesis of Compound XIII-10; Step 1: Synthesis of 4,6-dichloro-3-methyl-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4- d]pyrimidine (2); 4,6-dichloro-3-methyl-l H-pyrazolo[3,4-d]pyrimidine (1, 2 g, 9.85 mmol) was taken in ethyl acetate ( 100 mL), 3,4-Dihydropyran (2.5 g, 29.55 mmol) and p-TSA (0.1 g) were added to it. Reaction was stirred at RT for overnight. Product was detected by ESMS and NMR. Reaction was basified with Sat. NaHC03, organic layer was seperated, dried over sodium sulfate and concentrated to get 4,6- dichloro-3-methyl-l -(tetrahydro-2H-pyran-2-yl)-l H-pyrazolo[3,4-d]pyrimidine (2, 2.6 g, 92%). Crude product was used as such for the next step. NMR (400 MHz, CDC13): delta 5.95 (dd, 1 H), 4.18-4.10 (dd, 1 H), 3.83-3.76 (t, 1 H), 3.70 (s, 3H), 2.60-2.50 (m, 1H), 2.18-2.10 (m, 1H), 1.92- 1.60 (m, 4H).
  • 2
  • [ 1211522-68-7 ]
  • [ 1346447-98-0 ]
  • 3
  • [ 1211522-68-7 ]
  • [ 1346447-99-1 ]
  • 4
  • [ 1211522-68-7 ]
  • [ 1346448-00-7 ]
  • 5
  • [ 1211522-68-7 ]
  • C29H32N8O4 [ No CAS ]
  • 6
  • [ 1211522-68-7 ]
  • (4-((4-ethoxy-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3-methoxyphenyl)(morpholino)methanone [ No CAS ]
  • 7
  • [ 64-17-5 ]
  • [ 1211522-68-7 ]
  • 6-chloro-4-ethoxy-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of ethanol (0.227 g, 4.93 mmol) in THF (60 mL) was added sodium hydride inice bath. After stirred for 20 mm, 4, 6-dichloro-3-methyl-1H-pyrazolo [3,4-d]pyrimidine (1 g,4.93 mmol) was added. The mixture was gradually allowed to room temperature and stirredovernight at room temperature. The mixture was then diluted with water (20 mL),concentrated to remove solvent and diluted with ethyl acetate (220 mL). The organic layerwas washed with water (60 mLx 2), dried over Na2SO4, filtered and concentrated. The crudeproduct (900 mg, 86% yield) was directly used into next step.LCMS: 213[M+H]. tR=2.775 (LCMS condition 1)
  • 8
  • [ 64-17-5 ]
  • [ 1211522-68-7 ]
  • 6-chloro-4-ethoxy-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of ethanol (0.227 g, 4.93 mmol) in THF (60 mL) was added sodium hydride(0.591, 14.78 mmol) in ice bath. After 20 mi 4,6-dichloro-3-methyl-1H-pyrazolo-[3,4-d]-pyrimidine (Ig, 4.93 mmol) was added. The reaction mixture was gradually warmed to room temperature and then stirred overnight. Then, the mixture was diluted with water (20 mL), concentrated to remove solvent and diluted with ethyl acetate (220 mL). The organic layer was washed with water (60 mL x2), dried over Na2SO4, filtered and concentrated. The crudewas used in next step without further purification. Yield: 86%.LCMS: 213 [M+H]. tR 2.775 mins. (LCMS condition 1)
  • 9
  • [ 188111-79-7 ]
  • [ 1211522-68-7 ]
  • tert-butyl (R)-3-((6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.3% With N-ethyl-N,N-diisopropylamine; In ethanol; at 110.0℃; for 12.0h; After 4,6-dicMoro-3-memyl-lH-pyrazolo[3,4-d]pyrimidine (300.0 mg, 1.5 mmol) was dissolved in ethanol (10 mL), N,N-disopropylethylarnine (695.0 L, 2.2 mmol) and tert-butyl (R)-3-aminopiperidine-l-carboxylate (355.0 mg, 1.8 mmol) were added thereto. The reaction mixture was stirred at 110 C for 12 hours, and then the organic layer was isolated, treated with magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was isolated by column chromatography to obtain a title compound (414.5 mg, yield: 76.3%). (1398) NMR (500MHz, CD3OD) delta 4.59-4.50(m, 1H), 4.30-4.24(m, 1H), 3.93-3.89(m, 1H), 3.72-3.67(m, 1H), 3.19-3.17(m, 1H), 2.59(s, 3H), 2.10-2.00(m, 1H), 1.88-1.77(m, 2H), 1.63-1.30(m, 10H)
  • 10
  • [ 1211522-68-7 ]
  • N-((1s,4s)-4-((6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)acrylamide [ No CAS ]
  • 11
  • [ 1211522-68-7 ]
  • N-((1s,4s)-4-((3-methyl-6-((4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)acrylamide [ No CAS ]
  • 12
  • [ 1211522-68-7 ]
  • N-((1s,4s)-4-((3-methyl-6-((4-morpholinophenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)acrylamide [ No CAS ]
  • 13
  • [ 1211522-68-7 ]
  • N-((1s,4s)-4-((3-methyl-6-((4-(piperidin-1-yl)phenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)acrylamide [ No CAS ]
  • 14
  • [ 1211522-68-7 ]
  • N-((1s,4s)-4-((3-methyl-6-((4-(piperidin-1-yl)phenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)acrylamide [ No CAS ]
  • 15
  • [ 1211522-68-7 ]
  • 1-(6-((6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole[3,4-d]pyrimidin-4-yl)amino)indolin-1-yl)prop-2-en-1-one [ No CAS ]
  • 16
  • [ 1211522-68-7 ]
  • 1-(6-((3-methyl-6-(4-phenoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)indolin-1-yl)prop-2-en-1-one [ No CAS ]
  • 17
  • [ 1211522-68-7 ]
  • 1-(6-((3-methyl-6-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)indolin-1-yl)prop-2-en-1-one [ No CAS ]
  • 18
  • [ 1211522-68-7 ]
  • 6-chloro-3-methyl-N-(4-morpholinophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
  • 19
  • [ 1211522-68-7 ]
  • 3-methyl-N4-(4-morpholinophenyl)-N6-(3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole[3,4-d]pyrimidine-4,6-diamine [ No CAS ]
  • 20
  • [ 1211522-68-7 ]
  • N6-(3-aminophenyl)-3-methyl-N4-(4-morpholinophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine [ No CAS ]
  • 21
  • [ 1211522-68-7 ]
  • N-(3-((3-methyl-4-((4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)phenyl)acrylamide [ No CAS ]
  • 22
  • [ 5417-82-3 ]
  • [ 1211522-68-7 ]
  • 23
  • [ 5453-07-6 ]
  • [ 1211522-68-7 ]
  • 24
  • [ 2942-50-9 ]
  • [ 1211522-68-7 ]
YieldReaction ConditionsOperation in experiment
70 mg With phosphorus pentachloride; trichlorophosphate; for 12.0h;Reflux; 3-Methyl-1H-pyrazolo [3,4-d] pyrimidine-4,6-diol (100 mg, 0.60 mmol) was added to POCl3 (10 mL) PCl5 (417 mg, 2.0 mmol) was added. The reaction solution was refluxed for 12 hours, When the reaction is complete, the reaction is added to ice water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, and the desired compound was obtained by column chromatography. (70 mg)
  • 25
  • [ 1211522-68-7 ]
  • tert-butyl ((trans)-4-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)carbamate [ No CAS ]
  • 26
  • [ 1211522-68-7 ]
  • tert-butyl ((trans)-4-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)carbamate [ No CAS ]
  • 27
  • [ 1211522-68-7 ]
  • ((S)-1-(1-((trans)-4-aminocyclohexyl)-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol hydrochloride [ No CAS ]
  • 28
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-1-cyclohexyl-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
  • 29
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-1-cyclohexyl-3-methyl-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine [ No CAS ]
  • 30
  • [ 1211522-68-7 ]
  • (S)-(1-(1-cyclohexyl-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol hydrochloride [ No CAS ]
  • 31
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-1-cyclopentyl-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
  • 32
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-1-cyclopentyl-3-methyl-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine [ No CAS ]
  • 33
  • [ 1211522-68-7 ]
  • (S)-(1-(1-cyclopentyl-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol hydrochloride [ No CAS ]
  • 34
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-1-cyclobutyl-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
  • 35
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-1-cyclobutyl-3-methyl-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine [ No CAS ]
  • 36
  • [ 1211522-68-7 ]
  • (S)-(1-(1-cyclobutyl-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
  • 37
  • [ 1211522-68-7 ]
  • tert-butyl ((cis)-3-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclobutyl)carbamate [ No CAS ]
  • 38
  • [ 1211522-68-7 ]
  • tert-butyl ((cis)-3-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclobutyl)carbamate [ No CAS ]
  • 39
  • [ 1211522-68-7 ]
  • ((S)-1-(1-((cis)-3-aminocyclobutyl)-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
  • 40
  • [ 1211522-68-7 ]
  • tert-butyl ((trans)-3-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclobutyl)carbamate [ No CAS ]
  • 41
  • [ 1211522-68-7 ]
  • tert-butyl ((trans)-3-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclobutyl)carbamate [ No CAS ]
  • 42
  • [ 1211522-68-7 ]
  • ((S)-1-(1-((trans)-3-aminocyclobutyl)-3-methyl-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
  • 43
  • [ 1211522-68-7 ]
  • 4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
  • 44
  • [ 1211522-68-7 ]
  • 4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-3-methyl-1-(tetrahydrofuran-3-yl)-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine [ No CAS ]
  • 45
  • [ 1211522-68-7 ]
  • ((2S)-1-(3-methyl-1-(tetrahydrofuran-3-yl)-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
  • 46
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
  • 47
  • [ 1211522-68-7 ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine [ No CAS ]
  • 48
  • [ 1211522-68-7 ]
  • (S)-(1-(3-methyl-1-(tetrahydro-2H-pyran-4-yl)-6-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyrrolidin-2-yl)methanol hydrochloride [ No CAS ]
  • 49
  • [ 1211522-68-7 ]
  • (S)-2-((tert-butyldimethylsilyloxy)methyl)pyrrolidine hydrochloride [ No CAS ]
  • (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 2.0h; To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 - 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 - 3.82 (m, 1H), 3.72 - 3.39 (m, 2H), 2.22 - 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).
  • 50
  • [ 1211522-68-7 ]
  • (R)-2-((tert-butyldimethylsilyloxy)methyl)pyrrolidine hydrochloride [ No CAS ]
  • (R)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 20.0℃; for 3.0h; General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 - 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 - 3.82 (m, 1H), 3.72 - 3.39 (m, 2H), 2.22 - 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).
  • 51
  • [ 288315-03-7 ]
  • [ 1211522-68-7 ]
  • 6-chloro-4-(3,3-difluoroazetidin-1-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 3.0h; To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 - 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 - 3.82 (m, 1H), 3.72 - 3.39 (m, 2H), 2.22 - 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).
  • 52
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  • 2-[[2-([6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino)ethyl](methyl)amino]ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.78% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; ii (ii) 2-[[2-([6-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4- yl]amino)ethyl](methyl)amino]ethanol Into a 50-mL round-bottom flask, was placed 4,6-dichloro-3-methyl-1H-pyrazolo[3,4- djpyrimidine (240.00 mg, 1.182 mmol, 1.00 equiv), DCM (10.00 mL), DIEA (458.33 mg, 3.546 mmol, 3 equiv), 2-[(2-aminoethyl)(methyl)amino]ethanol (209.55 mg, 1.773 mmol, 1.50 equiv). The resulting solution was stirred for 16 hr at room temperature. The resulting mixture was concentrated. The solid was washed with EA and MeOH(10/1). The solids were collected by filtration. This resulted in 220 mg (60.78%) of 2-[[2-([6-chloro-3-methyl· 1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino)ethyl](methyl)amino]ethanol as a white solid. LCMS: (ES, m/z): [M+H]+ = 285
  • 53
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  • 5-chloro-N-{2-chloro-4-[4-({2-[(2-hydroxyethyl)(methyl)amino]ethyl}amino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}-2-fluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C 2: Cs2CO3; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane; lithium hydroxide monohydrate / 16 h / 100 °C / Inert atmosphere
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