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CAS No.: | 172015-79-1 |
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Name: | (1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C11H13Cl2N5O |
Molecular Weight: | 302.163 |
Synonyms: | (1S-cis)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol Monohydrochloride;ZLD0252;V2106;(1S,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride;((1S,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride; |
Melting Point: | 165-170?C |
Boiling Point: | 572oC at 760 mmHg |
Flash Point: | 299.7oC |
PSA: | 89.85000 |
LogP: | 2.55460 |
(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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With hydrogenchloride; orthoformic acid triethyl ester In water for 4h; Cyclization; | 92% |
With hydrogenchloride; orthoformic acid triethyl ester In water at 0 - 10℃; for 1h; Concentration; Temperature; | 76% |
With hydrogenchloride; orthoformic acid triethyl ester In ethanol at 0 - 10℃; for 10h; | 72.2% |
orthoformic acid triethyl ester
(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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With hydrogenchloride In tetrahydrofuran; industrial methylated spirit; water at 0 - 25℃; Product distribution / selectivity; | 82% |
With hydrogenchloride In industrial methylated spirit; water at 0 - 25℃; Product distribution / selectivity; | 81% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 1.264 g / tetrahydrofuran; H2O / 18 h / 20 - 60 °C 2: 90.5 percent / LiAlH4 / tetrahydrofuran / 19.5 h / 0 °C / Heating 3: 83 percent / Et3N / ethanol / 7 h / Heating 4: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme |
(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 83 percent / Et3N / ethanol / 7 h / Heating 2: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme |
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 83 percent / Et3N / ethanol / 7 h / Heating 2: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / ethanol / 0.5 h / 20 °C / Inert atmosphere 1.2: 3 h / 75 - 80 °C / Inert atmosphere 2.1: orthoformic acid triethyl ester; hydrogenchloride / ethanol / 10 h / 0 - 10 °C View Scheme |
2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 72 percent / aq. phosphate buffer / 4 h / pH 3.2 / Heating 2: 83 percent / Et3N / ethanol / 7 h / Heating 3: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme |
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90.5 percent / LiAlH4 / tetrahydrofuran / 19.5 h / 0 °C / Heating 2: 83 percent / Et3N / ethanol / 7 h / Heating 3: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme |
4,6-dichloro-2,5-diformamido-pyrimidine
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
Conditions | Yield |
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Stage #1: (1S,4R)-4-amino-2-cyclopentene-1-methanol tartrate salt With sodium carbonate In ethanol for 0.5h; Stage #2: 4,6-dichloro-2,5-diformamido-pyrimidine In ethanol for 3h; Heating / reflux; Stage #3: With hydrogenchloride; orthoformic acid triethyl ester more than 3 stages; |
Cyclopropylamine
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
abacavir
Conditions | Yield |
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In methanol at 70℃; for 12h; Substitution; | 90% |
Stage #1: (1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride With triethylamine In water Stage #2: Cyclopropylamine In water at 70 - 75℃; Concentration; Solvent; Temperature; | 90% |
In isopropyl alcohol at 90 - 95℃; for 12h; sealed reactor; | |
In ethanol at 25 - 78℃; for 6h; | |
With sodium carbonate In ethanol at 70 - 80℃; | 25 g |
pyrographite
Cyclopropylamine
((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride
abacavir
Conditions | Yield |
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With sodium hydroxide In acetone | 90% |