1306829-95-7|3-Bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine| Ambeed

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Quality Control of [ 1306829-95-7 ] Purity: 95% SDS Specification

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Product Details of [ 1306829-95-7 ]

CAS No. :	1306829-95-7
Formula :	C₆H₅BrN₄S
M.W :	245.10
SMILES Code :	CSC1=NC=C2C(NN=C2Br)=N1
MDL No. :	MFCD22415216
InChI Key :	PBEIXBIKEFRPGU-UHFFFAOYSA-N
Pubchem ID :	53375434

Safety of [ 1306829-95-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1306829-95-7 ]

* 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 [ 1306829-95-7 ]

[ 1306829-95-7 ] Synthesis Path-Downstream 1~42

1
[ 107-10-8 ]
[ 1306829-95-7 ]
[ 1306829-96-8 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a mixture of 3-bromo-6-(methylthio)-lH-pyrazolo[3,4-i/] pyrimidine (0.49 g, 2.0 mmol) in THF (5 mL) was added met -chloroperoxybenzoic acid (0.52 g, 99%, 3 mmol) at room temperature. The white mixture was stirred for 2 h and ^-propylamine (0.82 mL, 10 mmol) was added at 0 C. The resulting solution was heated at 40 C for 12 h. After removal of the solvent, MeOH was added and the mixture was filtered. The white solid was washed with MeOH (3x) and dried to provide 3-bromo-N-propyl-lH-pyrazolo[3,4-iif]pyrimidin-6- amine (0.45 g, 88%) as a white solid. 1H NMR (400 MHz, DMSO-^6) δ 13.19 (bs, 1H), 8.63 (s, 1H), 7.69 (bs, 1H), 3.29-3.17 (m, 2H), 1.61 - 1.49 (m, 2H), 0.88 (t, J = 7.4 Hz, 3H); 13C NMR (100 MHz, DMSO-t/6) δ 161.61, 156.98, 152.71, 120.06, 106.66, 42.68, 21.72, 11.47; MS m/z 256.1 [M+l].

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]Patent: WO2011/146313,2011,A1 .Location in patent: Page/Page column 57.

2
[ 1306829-95-7 ]
C₁₅H₁₆BrN₅ [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

3
[ 1306829-95-7 ]
C₁₄H₁₅BrN₆ [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

4
[ 1306829-95-7 ]
[ 1306830-00-1 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[3]Patent: WO2011/146313,2011,A1 .

5
[ 1306829-95-7 ]
[ 1306830-01-2 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

6
[ 1306829-95-7 ]
[ 1306830-02-3 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

7
[ 1306829-95-7 ]
[ 1306830-03-4 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

8
[ 1306829-95-7 ]
[ 1306830-04-5 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

9
[ 1306829-95-7 ]
[ 1306830-05-6 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

10
[ 1306829-95-7 ]
[ 1306830-06-7 ]

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11
[ 1306829-95-7 ]
[ 1306830-07-8 ]

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12
[ 1306829-95-7 ]
[ 1306830-08-9 ]

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13
[ 1306829-95-7 ]
[ 1306830-09-0 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

14
[ 1306829-95-7 ]
[ 1306830-10-3 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

15
[ 1306829-95-7 ]
[ 1306830-11-4 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

16
[ 1306829-95-7 ]
[ 1306830-12-5 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

17
[ 1306829-95-7 ]
[ 1306830-13-6 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

18
[ 1306829-95-7 ]
[ 1306830-14-7 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

19
[ 1306829-95-7 ]
[ 1306830-15-8 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

20
[ 1306829-95-7 ]
[ 1306830-16-9 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

21
[ 1306829-95-7 ]
[ 1306830-17-0 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

22
[ 1306829-95-7 ]
[ 1306830-18-1 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

23
[ 1306829-95-7 ]
[ 1306830-19-2 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

24
[ 1306829-95-7 ]
[ 1306830-20-5 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

25
[ 1306829-95-7 ]
[ 1306830-21-6 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

26
[ 1306829-95-7 ]
[ 1306830-22-7 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

27
[ 1306829-95-7 ]
[ 1306830-23-8 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

28
[ 1306829-95-7 ]
[ 1306830-24-9 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

29
[ 1306829-95-7 ]
C₆H₅BrN₄OS [ No CAS ]
3-bromo-6-(methylsulfonyl)-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

30
[ 1306829-95-7 ]
C₁₅H₁₆N₄OS [ No CAS ]
C₁₅H₁₆N₄O₂S [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

31
[ 1306829-95-7 ]
[ 1306829-99-1 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

32
[ 1306829-95-7 ]
C₁₄H₂₀BrN₅ [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

33
[ 1306829-95-7 ]
C₁₁H₁₆BrN₅ [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

34
[ 1306829-95-7 ]
C₁₉H₂₉BrN₆O₂ [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

35
[ 1306829-95-7 ]
C₁₄H₂₁BrN₆ [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

36
[ 1306829-95-7 ]
C₁₃H₂₀BrN₅O [ No CAS ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

37
[ 75-29-6 ]
[ 1306829-95-7 ]
[ 1306829-98-0 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.

38
[ 1306829-95-7 ]
[ 98-80-6 ]
[ 1306829-97-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 150℃; for 0.333333h;microwave irradiation;	A microwave tube was charged with 3-bromo-6-(methylthio)-lH-pyrazolo[3,4- d]pyrimidine (1.0 g, 4.0 mmol), phenylboronic acid (1.5 g, 12 mmol), potassium phosphonate (2.5 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0.35 g, 0,30 mmol), dioxane (16 mL) and water (4 mL) . The mixture was heated in microwave at 150 C for 20 min. The reaction mixture was poured into water. The aqueous layer was extracted with EtOAc (10X). The combined organic layer was dried (Na2S04), concentrated, and purified to provide 6- (methylthio)-3-phenyl-lH-pyrazolo[3,4-d]pyrimidme (0.85 g, 87%) as a white solid. MS m/z 243.1 [M+Hf.

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 129 - 134.
[3]Patent: WO2011/146313,2011,A1 .Location in patent: Page/Page column 35.

39
[ 5909-24-0 ]
[ 1306829-95-7 ]

References: [1]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[2]Patent: WO2015/25025,2015,A1 .
[3]Patent: WO2017/37146,2017,A1 .
[4]Patent: WO2020/10210,2020,A1 .

40
[ 100047-42-5 ]
[ 1306829-95-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With phosphorus(V) oxybromide; at 110℃; for 3h;Inert atmosphere;	A mixture of 6-(methylsulfanyl)-1H,2H,3H-pyrazolo[3,4-d]pyrimidin-3-one (45 g, 247 mmol) and phosphoroyl tribromide (566 g, 1.97 mol) was stirred for 3 h at 110 oC under nitrogen atmosphere. After cooling down to room temperature, the resulting mixture was triturated with ethyl ether (500 mL). The solids were collected by filtration and washed with ethyl ether (2 x 100 mL). The filter cake was then triturated with ice/water (3 L). The pH value of the mixture was adjusted to pH = 5 with concentrated aqueous solution of ammonia. The resulting mixture was filtered. The filter cake was washed with water (3 x 200 mL) and dried to afford 3-bromo-6- (methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine (55 g, 91%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) d 14.22 (br s, 1H), 9.01 (s, 1H), 2.57 (s, 3H). LC/MS (ESI, m/z): [(M + 1)]+ = 245.15, 247.15
77%		To a suspension of 6-(methylthio)-lH-pyrazolo[3,4-d]pyrimidin-3(2H)-one (0.50 g, 2.7 mmol) in CH3CN (15 mL) was added a C¾CN solution of P(0)Br3 (1.57 g, 5.5 mmol) in a pressure vessel. The mixture was sonicated for 30 min before being heated to 100 C for 16 h (overnight). After it was cooled to 0 C, H20 and aqueous ammonium hydroxide were added to basify the mixture. The mixture was stirred at 0 C for lh. The aqueous layer was extracted with EtOAc (10X). The combined EtOAc layer was dried (Na2S04), and concentrated to give 3-bromo-6-(methylthio)-l//-pyrazolo[3,4-d] pyrimidine (0.51 g, 77%) as a brown solid. NMR (400MHz, DMSO-t 6) δ: 9.00 (s, 1H), 5.57 (s, 3H); MS m/z 245.00 [M+H]+.
40%		A mixture of 6-methylsulfanyl-1,2-dihydro-pyrazolo[3,4-d]pyrimidin-3-one (4.5 g) and POBr3 (21.21 g) was heated in a sealed tube to 170C for 8 h. The reaction mixture was cooled to 25C, diluted with water and basified with 25% aq. ammonia solution and was then extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2504, filtered andevaporated under reduced pressure to afford the title compound (2.41 g, 40%) as a light brown solid. MS (ESI): mlz = 245.1 [M+H].

16%

With phosphorus(V) oxybromide; In acetonitrile; at 20 - 100℃; for 16.5h;Sonication;

A suspension of 6-(methylsulfanyl)- 1 H-pyrazolo [3 ,4-d]pyrimidin-3-ol (2 g, 10.98 mmol, 1.00 equiv) and phosphorus oxybromide (6.3 g, 21.98 mmol, 2.00 equiv) in acetonitrile (50 mL) was sonicated for 30 mm at room temperature. The resulting solution was allowed to react for anadditional 16 hours while the temperature was maintained at 100 C. The pH value of the solution was adjusted to 8 with ammonium hydroxide (25 %). The resulting mixture was concentrated under vacuum, diluted with ethyl acetate, and the solids were filtered out. The resulting solution was extracted with ethyl acetate and the organic layers were combined. The residue was purified by a silica gel column with dichloromethane/petroleum ether (100:0) to give 430 mg (16 %) of thetitle compound as a white solid. LC-MS (ES, m/z): 245, 247 [M+H].

References: [1]Patent: WO2020/10210,2020,A1 .Location in patent: Paragraph 00702; 00949.
[2]Patent: WO2011/146313,2011,A1 .Location in patent: Page/Page column 15; 16.
[3]ACS Combinatorial Science,2011,vol. 13,p. 414 - 420.
[4]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 129 - 134.
[5]Patent: WO2017/37146,2017,A1 .Location in patent: Page/Page column 250.
[6]Patent: WO2015/25025,2015,A1 .Location in patent: Page/Page column 382.

41
[ 1306829-95-7 ]
[ 1350550-48-9 ]

References: [1]Patent: WO2011/146313,2011,A1 .

42
[ 1306829-95-7 ]
[ 1350550-42-3 ]

References: [1]Patent: WO2011/146313,2011,A1 .
[2]Patent: WO2011/146313,2011,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nucleophilicity of Sulfur Compounds • Oxidation States of Sulfur Compounds • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 1306829-95-7 ]

Bromides

A649114 [1378860-94-6]

3-Bromo-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

Similarity: 0.81

Sulfides

A649114 [1378860-94-6]

3-Bromo-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

Similarity: 0.81

Related Parent Nucleus of
[ 1306829-95-7 ]

Other Aromatic Heterocycles

A649114 [1378860-94-6]

3-Bromo-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

Similarity: 0.81

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H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1306829-95-7

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