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6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

6-Chloro-1H-pyrazolo[3,4-d]pyrimidine structure

CAS No:
23002-51-9
Formula:
C5H3ClN4
Chemical Name:
6-Chloro-1H-pyrazolo[3,4-d]pyrimidine
Synonyms:
6-Chloro-1H-pyrazolo[3,4-d]pyrimidine;1H-Pyrazolo[3,4-d]pyriMidine, 6-chloro-;6-chloro-1(2)H-pyrazolo[3,4-d]pyrimidine;23002-51-9
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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6-Chloro-1H-pyrazolo[3,4-d]pyrimidine Basic Attributes

Molecular Weight：

154.56

Exact Mass：

154.004623

DSSTox ID：

DTXSID30680576

HScode：

2933990090

Characteristics

PSA：

54.5

XLogP3：

1.1

Density：

1.7±0.1 g/cm3

Flash Point：

167.0±8.5 °C

Refractive Index：

1.740

Safety Information

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

6-Chloro-1H-pyrazolo[3,4-d]pyrimidine Use and Manufacturing

Methods of Manufacturing

Compound 75 (2.0g, 11.3mmol) dissolved in THF (10mL), and at 0 was added hydrazine hydrate (1.33g, 22.6mmol) in THF (20mL) added and the reaction was stirred at room temperature for half hour and purified by silica gel column to give compound 76 as a yellow solid (1.0g, 57percent).Preparation No.2: 6-Chloro-l/ -pyrazolo[3, 4-i/|pyrimidine; A solution of 2, 4-dichloropyrimidine-5-carbaldehyde (7.75 g, 43.8 mmol, Preparation No.1) in THF (100 mL) was added to a 500 mL round-bottomed flask charged with anhydrous hydrazine (3.0 mL, 96 mmol) in THF (250 mL). The reaction mixture was allowed to stir at ambient temperature for about 1 h after which the reaction mixture was concentrated under reduced pressure. The crude product was suspended in DCM (100 mL) and filtered through a silica gel pad. The silica gel pad was washed with additional DCM (2 x 20 mL) and the combined organic layers were concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 30percent EtOAc in heptane to provide 6-chloro-lH-pyrazolo[3, 4- djpyrimidine (2.3 g, 34percent) as a white solid. LC/MS (Table 2, Method a) R, = 1.29 min; MS m/z: 155 (M+H)

Uses

Pyrazolo[3,4-d]pyrimidines have a close structural resemblanceto the substrates for the enzyme xanthine oxidase, hypoxanthine (6-hydroxypurine) and xanthine (2,6-dihydroxypurine). These compounds are capable of binding to the enzyme and strongly inhibit its activity.They have been studied for their role in the treatment and prophylaxis of hyperuricemia in human patients as well as potential anti-tumor agents.

Computed Properties

Molecular Weight:154.56
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:154.0046238
Monoisotopic Mass:154.0046238
Topological Polar Surface Area:54.5
Heavy Atom Count:10
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

CAS No.: 23002-51-9

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Guide of 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

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