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Chemistry
Heterocyclic Building Blocks
Pyrimidines
pyrrolopyrimidine
(S)-4-Oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid
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pyrrolopyrimidine

[ CAS No. 1190392-22-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1190392-22-3
Chemical Structure| 1190392-22-3
Chemical Structure| 1190392-22-3
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Quality Control of [ 1190392-22-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1190392-22-3 ]

CAS No. :1190392-22-3 MDL No. :MFCD20133989
Formula : C8H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VBGNTNJINOCQNQ-YFKPBYRVSA-N
M.W : 180.16 Pubchem ID :57907501
Synonyms :

Safety of [ 1190392-22-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1190392-22-3 ]

* 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 [ 1190392-22-3 ]

[ 1190392-22-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1190392-23-4 ]
  • [ 1190392-22-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl [6(S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-α]]pyrimidine-6-carboxylate With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water 5.B Step B: [(6S)-4-oxo-4,6 .8-tetrahydropyrrplo l,2-a]pyrimidine-6-carboxylic acid; Methyl [6(S)-4-oxo-4,6,7f8~tetrahydropyrrolo[ 1 ;2-a]pyrimidine-6-carboxylate (9.95 g, 51.2 mmol) in tetrahydrofuran (60 mL), methanol (40 mL) and a solution of lithium hydroxide (3.32g, 77 mmol) in water (40 mL) was stirred at ambient temperature for 1 h. 2 N hydrochloric acid (38.5 mL) was added to neutralize the reaction mixture which was then directly purified by reverse phase HPLC (TMC Pro-Pac CI 8; 0-40% 0.1 % trifluoroacetic acid in acetonitriie/ 0.1% trifluoroacetic acid in water gradient). The O-alkylation product was eluted fast. The pure fractions were collected and lyophilized overnight afforded the title compound as a pale yellow solid. 3H NMR (DMSO-i¾): δ 7.89 (d, J - 6.6 Hz, 1H), 6.24 (d, J - 6.6 Hz, 1H), 4.92 (dd, J - 10.0, 3.1 Hz, 1H), 3.12-2.99 (m, 2H), 2.52 (m, 1H), 2.11 (m, 1H). LC/MS 181.2 (M+l).
Stage #1: methyl [6(S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-α]]pyrimidine-6-carboxylate With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water B Methyl [6(1?)-4-oxo-4,6,738-tetrahydropyrrolo[lJ2-a]pyrimidine-6-carboxyiate (9.95 g, 51.2 mmol) in tetrahydrofuran (60 mL), methanol (40 mL) and a solution of lithium hydroxide (3.32g, 77 mmol) in water (40 mL) was stirred at ambient temperature for 1 h. 2 N hydrochloric acid (38.5 mL) was added to neutralize the reaction mixture which was then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The O-alkylation product was eluted fast The pure fractions were collected and lyophilized overnight to afford the title compound as a pale yellow solid. lH NMR (DMSO-ifc): δ 7.89 (d, J - 6.6 Hz, 1H), 6.24 (d, J - 6.6 Hz, 1H), 4.92 (dd, J = 10.0, 3.1 Hz, 1H), 3.12-2.99 (m, 2H), 2.52 (m, 1H), 2.11 (m, 1H). LC/MS 181.2 (M+l).
Stage #1: methyl [6(S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-α]]pyrimidine-6-carboxylate With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water 43.B Methyl [6(iS)-4-oxo-4,6s7,8-tetrahydropyrrolo[ 1 ,2-α]pyrimidine-6-carboxylate (9.95 g, 51.2 mmol) from step A in tetrahydrofuran (60 ml), methanol (40 ml) and a solution of lithium hydroxide (3.32g, 77 mmol) in water (40 ml) was stirred at ambient temperature for 1 h. 2 N hydrochloric acid (38.5 ml) was added to neutralize the reaction mixture which was then directly purified by reverse phase ηPLC (TMC Pro-Pac C 18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/ 0.1% trifluoroacetic acid in water gradient). The O-alkylation product was eluted fast. The pure fractions were collected and lyophilized overnight afforded the title compound as a pale yellow solid. 1H NMR (DMSO-d6) δ: 7.89 (d, J= 6.6 Hz, 1H), 6.24 (d, J= 6.6 Viz, 1H), 4.92 (dd, J= 10.0, 3.1 Hz, 1H), 3.12-2.99 (m, 2H)S 2.52 (m, 1H), 2.11 (m, 1H). LC/MS 181.2 (M+l)+.
Stage #1: methyl [6(S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-α]]pyrimidine-6-carboxylate With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water 44.B Methyl[6(S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-α]pyrimidine-6-carboxylate (9.95 g, 51.2 mmol) in tetrahydrofuran (60 mL), methanol (40 mL) and a solution of lithium hydroxide (3.32 g, 77 mmol) in water (40 mL) was stirred at ambient temperature for 1 h. 2 N hydrochloric acid (38.5 mL) was added to neutralize the reaction mixture which was then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The O-alkylation product was eluted fast. The pure fractions were collected and lyophilized overnight to afford the title compound as a pale yellow solid. 1H NMR (DMSO-d6): δ 7.89 (d, J=6.6 Hz, 1H), 6.24 (d, J=6.6 Hz, 1H), 4.92 (dd, J=10.0, 3.1 Hz, 1H), 3.12-2.99 (m, 2H), 2.52 (m, 1H), 2.11 (m, 1H). LC/MS 181.2 (M+1).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2012/12314, 2012, A1 Location in patent: Page/Page column 51
[2]Current Patent Assignee: MERCK & CO INC - WO2011/43942, 2011, A1 Location in patent: Page/Page column 33-34
[3]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1 Location in patent: Page/Page column 50-51
[4]Current Patent Assignee: MERCK & CO INC - US2009/253705, 2009, A1 Location in patent: Page/Page column 41
  • 2
  • [ 173142-47-7 ]
  • [ 1190392-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 110 °C 2: water; lithium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 110 °C 2: water; lithium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 110 °C 2: water; lithium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2012/12314, 2012, A1
[2]Current Patent Assignee: MERCK & CO INC - WO2011/43942, 2011, A1
[3]Current Patent Assignee: MERCK & CO INC - US2009/253705, 2009, A1
  • 3
  • [ 1190391-85-5 ]
  • [ 1190392-22-3 ]
  • [ 1190393-25-9 ]
YieldReaction ConditionsOperation in experiment
72% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2h; A To a solution of i-13a (21.4 g, 55.9 mmol) in N,N-dimethylformamide (100 ml) at 0 °C was added [(6iS)-4-oxo-4s6,7,8-tetrahydropyrrolo[is2-a]pyrimidine-6-carboxyUc acid (i-44, 11.1 g, 61.5 mmol), followed by 1-hydroxybenzotriazole (7.55 g, 55.9 mrnol), N-(3- dimethylaminopropyl)-A^-ethylcarbodiimide hydrochloride (16.1 gs 84.0 mmol) and NtN- diisopropylethyiamine (29.2 ml, 168 mmol). The reaction mixture was stirred from 0 °C to ambient temperature for 2 h. Water (600 ml) was added and it was extracted withdichloromethane (600 ml x 2). The combined organic layers were dried over Na2S04. After removal of the volatiles, the residue was purified by using a Biotage Horizon system (0-5% then 5% methanol with 10% ammonia/dichloromethane mixture) to afford the title compound which contained 8% of the minor diastereomer. It was further purified by supercritical fluid chromatography (chiral AS column, 40% methanol) to afford the -title compound as a pale yellow solid (22.0 g, 72%). 1H NM (CDC13): 6 9.61 (s, 1H), 7.93 (d, -J = 6:6 Hz, 1H), 7.49 (d, J = 8.4 Hz, 2H), 7.35-7.28 (m, 5H)S 7.13 (d, J = 8.5 Hz, 2H), 6.40 (d, J = 6.7 Hz, 1H)5 5.36 (d, J - 8.6 Hz, 1H), 4.38 (m, 1H)S 4.12-4.04 (m, 2H), 3.46 (m,lH), 3.15-3.06 (m, 2H), 2.91 (dd> J - 13.1, 9.0 Hz, 1H), 2.55 (m, 1H), 2.38 (m, 1H), 1.71-1.49 (m, 13H). LC-MS 567.4 (M+23).
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/43942, 2011, A1 Location in patent: Page/Page column 42-43
  • 4
  • [ 1190709-67-1 ]
  • [ 1190392-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.75 h / 150 °C 2: water; lithium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 0.75 h / 150 °C 2: water; lithium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/43942, 2011, A1
[2]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1

Tags: 1190392-22-3 synthesis path| 1190392-22-3 SDS| 1190392-22-3 COA| 1190392-22-3 purity| 1190392-22-3 application| 1190392-22-3 NMR| 1190392-22-3 COA| 1190392-22-3 structure

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pyrrolopyrimidine
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pyrrolopyrimidine
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Vibegron

Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Amide Hydrolysis • Amide Hydrolysis • Anhydride Hydrolysis • Arndt-Eistert Homologation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Esters Hydrolyze to Carboxylic Acids and Alcohols • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Hunsdiecker-Borodin Reaction • Nitriles Hydrolyze to Carboxylic Acids • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Amines • Preparation of Carboxylic Acids • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Amines • Reactions of Carboxylic Acids • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • The Conversion of Carboxylic Acids into Acyl Halides • Ugi Reaction
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