767-69-1

Usage

Uses

Used in Chemical Synthesis:
6-Bromopurine is used as a key intermediate in the synthesis of 6-halopurine alkynes and corresponding triazole derivatives, which are valuable compounds in organic chemistry and have potential applications in various fields.
Used in Pharmaceutical Research:
6-Bromopurine is used as a precursor in the synthesis and chemical characterization of 2,3,4,5-tetrahydro-1,5-benzoxazepines-3-ol, a class of compounds with potential therapeutic properties.
Used in Cancer Research:
6-Bromopurine enhances the carcinostatic activity of azaserine in a test system employing ascites cell forms of sarcoma 180 and Ehrlich carcinoma in vivo, indicating its potential use in cancer research and treatment.
Used in Organic Chemistry:
6-Bromopurine nucleosides are excellent substrates for substitution reactions with N-, O-, and S-containing nucleophiles in polar solvents, making them valuable in the development of new organic compounds and materials.

InChI:InChI=1/C5H3BrN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)

Synthetic route

3,4-dihydro-2H-pyran (110-87-2) + 6-bromopurine (767-69-1) → 6-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (381246-26-0)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 0 - 20℃; for 1h;	98%
toluene-4-sulfonic acid In chloroform at 0 - 20℃; for 18h;	94%

6-bromopurine (767-69-1) → 6-hydrazinyl-7H-purine (5404-86-4)

Conditions	Yield
With hydrazine hydrate In ethanol for 0.5h; Heating;	93%

rac-ethyl 5-((tert-butoxycarbonyl)oxy)cyclopent-1-ene-1-carboxylate + 6-bromopurine (767-69-1) → (R)-ethyl 5-(6-bromo-9H-purin-9-yl)cyclopent-1-ene-1-carboxylate

Conditions	Yield
Stage #1: 6-bromopurine With tris-(dibenzylideneacetone)dipalladium(0); (S,S)-[2-(4'-isopropyloxazolin-2'-yl)ferrocenyl]diphenylphosphine; α-naphthol; potassium carbonate In toluene at 20℃; for 0.5h; Inert atmosphere; Stage #2: rac-ethyl 5-((tert-butoxycarbonyl)oxy)cyclopent-1-ene-1-carboxylate In toluene at 0℃; for 72h; Inert atmosphere; enantioselective reaction;	93%

3-hepten-2-one (5609-09-6, 69668-88-8, 1119-44-4) + 6-bromopurine (767-69-1) → C12H15BrN4O (1438428-57-9)

Conditions	Yield
With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; benzoic acid In toluene at 25℃; for 48h; Catalytic behavior; Temperature; Michael Addition; enantioselective reaction;	89%

6-bromopurine (767-69-1) + 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (15397-15-6) → C32H25BrN4O7 (622379-84-4)

Conditions	Yield
Stage #1: 6-bromopurine With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 90℃; for 0.75h; Stage #2: 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 90℃; for 3.5h;	87%

2-(1-aminopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1262441-50-8) + 6-bromopurine (767-69-1) → 3-iodo-6-methyl-2-[1-(9H-purin-6-ylamino)propyl]-4H-pyrido[1,2-a]pyrimidin-4-one (1262441-51-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux; Inert atmosphere;	82.5%

6-bromopurine (767-69-1) + trimethylamine (75-50-3) → 6-Bromo-9H-purine; compound with trimethyl-amine

Conditions	Yield
In N,N-dimethyl-formamide Ambient temperature;	80%

(S)-3-phenyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (1403942-64-2) + 6-bromopurine (767-69-1) → (S)-2-(1-(9H-purin-6-yl)pyrrolidin-2-yl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1403946-84-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃;	80%

6-bromopurine (767-69-1) + methyl iodide (74-88-4) → 6-bromo-7-methyl-7H-purine (376628-24-9)

Conditions	Yield
Stage #1: 6-bromopurine With 2,2,6,6-tetramethylpiperidinylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 25℃; for 20h; Inert atmosphere;	80%

(S)-2-(1-((9H-purin-6-yl-2,8-d2)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one (870281-86-0) + 6-bromopurine (767-69-1) → CAL-101

Conditions	Yield
With sodium acetate; acetic acid In isopropyl alcohol at 80℃; for 18h;	78%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol

6-bromopurine (767-69-1) + 2-bromocyclopentanone (1056246-36-6) → 2-(6-bromo-9H-purin-9-yl)cyclopentan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	71%

2-ethylhexyl bromide (18908-66-2) + 6-bromopurine (767-69-1) → 6-bromo-9-ethylhexylpurine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h;	68%

diethyl 3-(phenyl)oxirane-2,2-dicarboxylate (58070-00-1) + 6-bromopurine (767-69-1) → diethyl 2-((6-bromo-9H-purin-9-yl)(phenyl)methoxy)malonate

Conditions	Yield
With yttrium(III) trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 10h; Molecular sieve; Sealed tube; regioselective reaction;	67%

6-bromopurine (767-69-1) + thymidine (50-89-5) → 6-bromo-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine

Conditions	Yield
With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose In aq. buffer at 30℃; pH=7; Green chemistry; Enzymatic reaction;	61%

(S)-2-(1-amino-1-d-propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one + 6-bromopurine (767-69-1) → (S)-2-(1-(9H-purin-6-yl-amino)-1-d-propyl)-5-fluoro-3-phenylquinazoline-4(3H)-ketone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃; for 30h;	60%

benzyl bromide (100-39-0) + 6-bromopurine (767-69-1) → 6-bromo-7-(phenylmethyl)-7H-purine + 6-bromo-9-(phenylmethyl)-9H-purine (869683-37-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 16h;	A 17% B 59%

1-[3-(3,5-difluorophenyl)-5-methylimidazo[1,2-a]pyridin-2-yl]ethanamine (1312585-53-7) + 6-bromopurine (767-69-1) → N-{1-[3-(3,5-difluorophenyl)-5-methylimidazo[1,2-a]pyridin-2-yl]ethyl}-9H-purin-6-amine (1312585-13-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 90℃; for 18h;	58%

1-[8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanamine (1312685-75-8) + 6-bromopurine (767-69-1) → N-{1-[8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethyl}-9H-purin-6-amine (1312685-76-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux; Inert atmosphere;	57%

6-bromopurine (767-69-1) + Ethyl nipecotate (71962-74-8) → ethyl 1-(9H-purin-6-yl)piperidine-3-carboxylate

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl acetamide at 100℃;	55%

(RS)-2,3-dihydro-1,4-benzoxathiin-2-methanol (35143-11-4) + 6-bromopurine (767-69-1) → (RS)-6-bromo-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purine (1020397-97-0) + (RS)-6-bromo-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine (1335000-20-8)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 140℃; for 0.0833333h; Mitsunobu reaction; Microwave irradiation;	A 6% B 54%

(R,S)-3-(3,4-dihydro-2H-1,5-benzoxathiepine-3-yloxy)propane-1-ol (1339200-58-6) + 6-bromopurine (767-69-1) → (R,S)-6-bromo-9-[3-(3,4-dihydro-2H-1,5-benzoxathiepine-3-yloxy)-propyl]-9H-purine (1339200-73-5)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 140℃; for 0.0833333h; Inert atmosphere; Cooling with ice; Microwave irradiation;	53%

7-(1-aminoethyl)-6-(3,5-difluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one + 6-bromopurine (767-69-1) → 6-(3,5-difluorophenyl)-3-methyl-7-[1-(9H-purin-6-ylamino)ethyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Conditions	Yield
Stage #1: 7-(1-aminoethyl)-6-(3,5-difluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one; 6-bromopurine With N-ethyl-N,N-diisopropylamine In ethanol at 110℃; Stage #2: With ammonium hydroxide	51%

(S)-1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)ethanamine (1393176-14-1) + 6-bromopurine (767-69-1) → (S)-N-(1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl)-9H-purin-6-amine (1393180-50-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃; for 72h;	50%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃; for 72h;	50%

racemic 2-(1-aminopropyl)-3-phenylpyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (1403942-28-8) + 6-bromopurine (767-69-1) → racemic 2-(1-(9H-purin-6-ylamino)propyl)-3-phenylpyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (1404199-25-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃; for 40h;	50%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃; for 40h;	50%

(S)-3-phenyl-2-(pyrrolidin-2-yl)-3H-imidazo[4,5-b]pyridine (1404085-15-9) + 6-bromopurine (767-69-1) → (S)-6-(2-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyrrolidin-1-yl)-9H-purine (1404086-36-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃;	49%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 80℃;	49%

6-bromopurine (767-69-1) + 1,2,3,5-tetraacetylribose (13035-61-5) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (74465-47-7)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 5h; Vorbruggen nucleosidation reaction; Inert atmosphere;	47%

(S)-7-(1-aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (1262441-70-2) + 6-bromopurine (767-69-1) + trifluoroacetic acid (76-05-1) → (S)-7-(1-(9H-purin-6-ylamino)ethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one trifluoroacetate

Conditions	Yield
Stage #1: (S)-7-(1-aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one; 6-bromopurine With N-ethyl-N,N-diisopropylamine In ethanol for 17h; Inert atmosphere; Reflux; Stage #2: trifluoroacetic acid	45.8%

(S)-2-(1-aminopropyl)-3-phenylpyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (1403942-17-5) + 6-bromopurine (767-69-1) → (S)-2-(1-(9H-purin-6-ylamino)propyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1403945-93-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 100℃; for 40h;	45%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 100℃; for 40h;	45%

(S)-2-(1-aminoethyl)-3-phenylpyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (1403942-30-2) + 6-bromopurine (767-69-1) → (S)-2-(1-(9H-purin-6-ylamino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1403946-02-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 100℃; for 40h;	45%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 100℃; for 40h;	45%

7-(1-aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one + 6-bromopurine (767-69-1) → 6-(3-fluorophenyl)-3-methyl-7-[1-(9H-purin-6-ylamino)ethyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Conditions	Yield
Stage #1: 7-(1-aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one; 6-bromopurine With N-ethyl-N,N-diisopropylamine In ethanol at 110℃; Stage #2: With ammonium hydroxide	44%

Upstream product

• 68-94-0 6-hydroxypurine 
• 68-94-0 1,7-dihydro-6H-purin-6-one 

Downstream Products

• 1126365-60-3 N-[2-methyl-5-(7H-purin-6-yl)phenyl]-4-(pyridin-2-ylmethoxy)benzamide 
• 870281-82-6 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]-3,4-dihydroquinazolin-4-one 
• 132194-25-3 6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 869683-37-4 6-bromo-9-(phenylmethyl)-9H-purine 
• 5404-86-4 6-hydrazinyl-7H-purine 
• 622379-84-4 C₃₂H₂₅BrN₄O₇ 
• 1200437-70-2 6-bromo-9-[3-(hydroxymethyl)phenyl]purine 
• 1265578-71-9 1-[(o-nitrophenyl)sulfonyl]-1,5-dihydro-4,1-benzoxazepin 
• 1265578-53-7 (RS)-6-bromo-9-[1-(o-nitrobenzenesulfonyl)-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]-9H-purine 
• 1265578-69-5 1-[(p-nitrophenyl)sulfonyl]-1,5-dihydro-4,1-benzoxazepin 
• 1265578-51-5 (RS)-6-bromo-9-[1-(p-nitrobenzenesulfonyl)-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]-9H-purine 

Relevant academic research and scientific papers

Synthetic method for 6-bromopurine

The invention discloses a synthetic method for 6-bromopurine. The synthetic method comprises the following steps: with hypoxanthine and phosphorus oxybromide as raw materials, subjecting the raw materials to a heating reflux reaction under the action of an organic solvent and a quaternary ammonium salt; and after completion of the reaction, carrying out vacuum filtration to remove liquid so as toobtain 6-bromopurine. The synthetic method of the invention reduces the usage of phosphorus oxybromide, lowers reaction temperature, shortens reaction time and reduces production cost of 6-bromopurine.