346599-63-1

Basic information

• Product Name: 4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one
• Synonyms: 4-Chloro-5,7-dihydro-6H-p...;3-d]pyriMidin-6(7H)-one;4-chloro-5H-pyrrolo[2;4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyriMidin-6-one;4-chloro-1,5-dihydro-6H-pyrrolo[2,3-d]pyriMidin-6-one;4-chloro-5H-pyrrolo[2,3-d]pyriMidin-6(7H)-one C6H4ClN3O 169.57;4-chloro-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one;4-chloro-1H-pyrrolo[2,3-d]pyrimidin-6(5H)-one
• CAS NO: 346599-63-1
• Molecular Formula: C₆H₄ClN₃O
• Molecular Weight: 169.57
• Product Categories: CHIRAL CHEMICALS
• Mol File: 346599-63-1.mol

Chemical Properties

• Boiling Point: 409.626 °C at 760 mmHg
• Flash Point: 201.535 °C
• Appearance: /
• Density: 1.549 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.12±0.20(Predicted)
• CAS DataBase Reference: 4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one(346599-63-1)
• EPA Substance Registry System: 4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one(346599-63-1)

Safety Data

• Hazardous Substances Data: 346599-63-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one is used as a key intermediate in the synthesis of pharmaceutical compounds for its potential therapeutic applications. It plays a crucial role in the development of new drugs, particularly in the area of oncology, where it has been studied for its anticancer properties.
Used in Agrochemical Industry:
4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one is used as a building block in the synthesis of agrochemical products, specifically as a herbicide. Its herbicidal properties make it a valuable component in the development of effective weed control solutions for agricultural applications.

InChI:InChI=1/C6H4ClN3O/c7-5-3-1-4(11)10-6(3)9-2-8-5/h2H,1H2,(H,8,9,10,11)

Upstream product

• 40967-67-7 trimethyl ethane-1,1,2-tricarboxylate 
• 1402550-59-7 methyl 2-(4-amino-6-chloropyrimidin-5-yl)acetate 
• 171096-33-6 methyl 2-(4,6-dichloropyrimidin-5-yl)acetate 
• 3680-71-5 7-deazahypoxanthine 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 346600-31-5 4-chloro-5-(3,5-dimethyl-1 H-pyrrol-2-ylmethylene)-5,7-dihydro-pyrrolo [2,3-d]pyrimidin-6-one 
• 346599-66-4 5-(6-OXO-4-PIPERIDIN-1-YL-6,7-DIHYDRO-PYRROLO [2,3-D]PYRIMIDIN-5-YLIDENEMETHYL)-1H-PYRROLE-2-CARBOXYLIC ACID (2-MORPHOLIN-4-YL-ETHYL)-AMIDE 
• 346600-29-1 4-chloro-5-[3,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrol-2-ylmethylene]-5,7-dihydro-pyrrolo [2,3-d]pyrimidin-6-one 
• 346600-09-7 5-[3-METHYL-5-(MORPHOLINE-4-CARBONYL)-1H-PYRROL-2-YLMETHYLENE]-4-PIPERIDIN-1-YL-5,7-DIHYDRO-PYRROLO [2,3-D]PYRIMIDIN-6-ONE 
• 346600-32-6 5-(4-chloro-6-oxo-6,7-dihydro-pyrrolo [2,3-d]pyrimidin-5-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide 
• 1093798-73-2 C₁₇H₂₆N₆O₃ 
• 1093798-79-8 C₁₈H₂₆N₆O₃ 
• 1093799-99-5 C₁₅H₂₃N₅O₃ 
• 1093799-30-4 C₂₀H₃₃N₇O₃ 
• 1093799-19-9 C₂₇H₃₇N₇O₃ 
• 1093799-41-7 C₂HF₃O₂*C₂₈H₃₈N₈O₅ 
• 1093800-27-1 C₂HF₃O₂*C₂₈H₃₁N₇O₅ 
• 1093799-09-7 C₂HF₃O₂*C₂₃H₂₇ClN₆O₄ 
• 1093798-85-6 C₃₁H₄₂FN₇O₅*ClH 

Relevant articles and documents

Novel Hinge-Binding Motifs for Janus Kinase 3 Inhibitors: A Comprehensive Structure-Activity Relationship Study on Tofacitinib Bioisosteres

The Janus kinases (JAKs) are a family of cytosolic tyrosine kinases crucially involved in cytokine signaling. JAKs have been demonstrated to be valid targets in the treatment of inflammatory and myeloproliferative disorders, and two inhibitors, tofacitinib and ruxolitinib, recently received their marketing authorization. Despite this success, selectivity within the JAK family remains a major issue. Both approved compounds share a common 7H-pyrrolo[2,3-d]pyrimidine hinge binding motif, and little is known about modifications tolerated at this heterocyclic core. In the current study, a library of tofacitinib bioisosteres was prepared and tested against JAK3. The compounds possessed the tofacitinib piperidinyl side chain, whereas the hinge binding motif was replaced by a variety of heterocycles mimicking its pharmacophore. In view of the promising expectations obtained from molecular modeling, most of the compounds proved to be poorly active. However, strategies for restoring activity within this series of novel chemotypes were discovered and crucial structure-activity relationships were deduced. The compounds presented may serve as starting point for developing novel JAK inhibitors and as a valuable training set for in silico models.

An efficient synthesis of 4-chloro-2-pyrrolino[2,3- d ]pyrimidin-6-one and its 7-substituted analogues

An efficient synthesis of 4-chloro-2-pyrrolino[2,3-d]pyrimidin-6-one was achieved in four steps starting from dimethyl malonate in 23% overall yield. This synthesis was demonstrated on 100 g scale to obtain 4-chloro-2-pyrrolino[2, 3-d]pyrimidin-6-one in 9

AKT AND P70 S6 KINASE INHIBITORS

The present invention provides AKT and p70 S6 kinase inhibitors of the formula: The present invention also provides pharmaceutical compositions comprising compounds of Formula I, uses of compounds of Formula I and methods of using compounds of Formula I.

SUBSTITUTED PIPERIDINES HAVING PROTEIN KINASE INHIBITING ACTIVITY

The invention provides PKA and PKB kinase-inhibiting compounds of the formula (I); or salts, solvates, tautomers or N-oxides thereof, wherein E is a five membered heteroaryl ring containing 1, 2, 3 or 4 heteroatoms selected from O, N and S provided that no more than 1 heteroatom may be other than N; q and r are each is 0 or 1; provided that q+r is 1 or 2; T is N or a group CR5; J1-J2 is N=C(R6), (R7)C=N, (R8)N- C(O), (R8)2C-C(O), N=N or (R7)C=C(R6); Q3 is a bond or a saturated C1-3 hydrocarbon linker group optionally substituted by fluorine and hydroxy; G is NR2R3, CN or OH; m and n are each 0 or 1, provided that m+n is 1 or 2, and provided also that m or n are each 0 when the adjacent ring member of ring E is S or O; R1a and R1b are the same or different and each is hydrogen or a substituent R10; or R1a and R1b together with the carbon atoms or heteroatoms to which they are attached form a 5 or 6-membered aryl or heteroaryl ring, wherein the aryl or heteroaryl rings are optionally substituted by one or more substituents R10; and R2, R3, R4, R5, R7, R6, R8, and R10 are as defined in the claims.

SPIROLACTAM TRICYCLIC CGRP RECEPTOR ANTAGONISTS

Compounds of formula (I): (wherein variables A1, A2, A3, A4, A5, A6, A7, B1, B2, B3, B4, D1, D2, E1, E2, E3, E4, E5, G1, G2, J, K, T, U, V, W, X, Y and Z are as described herein) which are antagonists of CGRP receptors and which are useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

SPIROLACTAM ARYL CGRP RECEPTOR ANTAGONISTS

Compounds of formula (I): (wherein variables A1, A2, A3, A4, A5, A6, A7, E1, E2, E3, E4, E5, G1, G2, J and K are as described herein) which are antagonists of CGRP receptors and which are useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

SPIROLACTAM BICYCLIC CGRP RECEPTOR ANTAGONISTS

Compounds of formula (I): (wherein variables A1, A2, A3, A4, A5, A6, A7, B, E1, E2, E3, E4, E5, G1, G2, J and K are as described herein) which are antagonists of CGRP receptors and which are useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

PHARMACEUTICAL COMPOUNDS

The invention provides compounds of the formula (I): or salts, solvates, tautomers or N-oxides thereof, wherein J1-J2 is CH=CH, N=CH, CH=N, HN-C(O) or CH2CO; T is N or CH and GP is as defined in the claims. The compounds have activity as inhibitors of PKA and PKB kinases and are useful in the treatment of cancers.

MONOCYCLIC ANILIDE SPIROLACTAM CGRP RECEPTOR ANTAGONISTS

The present invention is directed to compounds of Formula I: I (where variables A1, A2, B, J, K, m, n, R4, R5a, R5b and R5c are as defined herein) useful as antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

TRICYCLIC ANILIDE SPIROLACTAM CGRP RECEPTOR ANTAGONISTS

The present invention is directed to compounds of Formula I: I (where A1, A2, B1, B2, B3, B4, D1, D2, J, K, T, U, V, W, X, Y, Z, R4, R5a, R5b, R5c, m and n are defined herein) useful as antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.