18593-44-7|5,6-Dimethylthieno[2,3-d]pyrimidin-4(3H)-one| Ambeed

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Quality Control of [ 18593-44-7 ] Purity: 97% SDS Specification

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Product Details of [ 18593-44-7 ]

CAS No. :	18593-44-7
Formula :	C₈H₈N₂OS
M.W :	180.23
SMILES Code :	CC1=C(C)C2=C(S1)N=CNC2=O
MDL No. :	MFCD00463622
InChI Key :	QAFMGDDXMIKGEY-UHFFFAOYSA-N
Pubchem ID :	403053

Safety of [ 18593-44-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 18593-44-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	50.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	73.99 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.42
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.48
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.6
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.17
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.66
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.87

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.44
Solubility	0.647 mg/ml ; 0.00359 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.64
Solubility	0.412 mg/ml ; 0.00229 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.28
Solubility	0.095 mg/ml ; 0.000527 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.35 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.34

Application In Synthesis of [ 18593-44-7 ]

* 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 [ 18593-44-7 ]

[ 18593-44-7 ] Synthesis Path-Downstream 1~35

1
[ 109-65-9 ]
[ 18593-44-7 ]
[ 32973-73-2 ]

References: [1]Pharmazie,1983,vol. 38,p. 135 - 136.

2
[ 74-96-4 ]
[ 18593-44-7 ]
[ 86009-38-3 ]

References: [1]Pharmazie,1983,vol. 38,p. 135 - 136.

3
[ 539-74-2 ]
[ 18593-44-7 ]
[ 108311-84-8 ]

References: [1]Pharmazie,1986,vol. 41,p. 661 - 661.

4
[ 18593-44-7 ]
[ 109-70-6 ]
3-(3-Chloro-propyl)-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one [ No CAS ]

References: [1]Pharmazie,1983,vol. 38,p. 135 - 136.

5
[ 18593-44-7 ]
[ 106-95-6 ]
[ 50803-33-3 ]

References: [1]Pharmazie,1983,vol. 38,p. 135 - 136.

6
[ 32973-77-6 ]
[ 18593-44-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 432 - 433.

7
[ 99379-87-0 ]
[ 18593-44-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 432 - 433.

8
[ 4815-24-1 ]
[ 18593-44-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 432 - 433.

9
[ 18593-44-7 ]
[ 307512-33-0 ]

References: [1]Molecules,2010,vol. 15,p. 3932 - 3957.
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

10
[ 18593-44-7 ]
[ 927969-35-5 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

11
[ 18593-44-7 ]
[ 302952-45-0 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

12
[ 18593-44-7 ]
[ 442571-26-8 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

13
[ 18593-44-7 ]
[ 338425-01-7 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

14
[ 18593-44-7 ]
C₁₈H₁₈N₂O₂S₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

15
[ 18593-44-7 ]
C₁₃H₁₆N₂O₂S₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

16
[ 18593-44-7 ]
[ 442571-27-9 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

17
[ 18593-44-7 ]
[ 296262-16-3 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 870 - 876.

18
C₉H₁₅NO₂S [ No CAS ]
[ 77287-34-4 ]
[ 18593-44-7 ]

References: [1]Synthetic Communications,2011,vol. 41,p. 2835 - 2851.

19
[ 4584-46-7 ]
[ 18593-44-7 ]
[ 941556-66-7 ]

References: [1]Synthetic Communications,2011,vol. 41,p. 2835 - 2851.

20
[ 18593-44-7 ]
[ 1321891-03-5 ]

References: [1]Synthetic Communications,2011,vol. 41,p. 2835 - 2851.

21
[ 18593-44-7 ]
[ 108831-68-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With trichlorophosphate;Reflux;	General procedure: The different thieno[2,3-d]pyrimidin-4-one (6a-d or f-i) (1 eq.) and phosphoryl chloride (2.9 mL/mmoleq.) were refluxed for 8 h. The reaction mixture was then cooled in an ice-bath and carefully neutralised by the addition of aqueous saturated NaHCO3 solution. The resulting mixture was extracted with ethylacetate (15 mL/mmol eq.), the organic layer was separated, dried over MgSO4 and concentrated. The crude residue was purified by flash column chromatography eluting with n-hexane-EtOAc 100:0 v/vincreasing to n-hexane-EtOAc 85:15 v/v unless otherwise stated.
90.6%	With thionyl chloride; In N,N-dimethyl-formamide; for 3.0h;Reflux;	Take 1.8g (0.01mol) 5,6- dimethyl-thieno [2,3-d] pyrimidin -4 (3H) - one in 10ml of thionyl chloride, was added one drop of dimethyl formamide (DMF) was heated at reflux for 3 hours, monitored by TLC after completion of the reaction, the solvent was distilled off under reduced pressure to give a dark gray solid 1.8g, 90.6% yield, m.p. 112-113 .
80%	With phosphorus pentachloride; trichlorophosphate; at 105℃;	General procedure: A mixture of thienopyrimidinone (0.01 mol), POCl3 (11 mL) and PCl5 (1.5 g) was quickly heated to 105 C and boiled for 5-6 h. The solvent was evaporated. Dry product was dissolved in methylene chloride (12 mL) and neutralized by cold solution of NaOH (0.5 N). The organic phase was separated and dried over Na2SO4, filtered, and then solvent was evaporated in vacuum. The residue was crystallized from isopropyl alcohol. Yield 80%

References: [1]European Journal of Medicinal Chemistry,2016,vol. 123,p. 31 - 47.
[2]Patent: CN105218557,2016,A .Location in patent: Paragraph 0217; 0218; 0219.
[3]European Journal of Medicinal Chemistry,2016,vol. 115,p. 148 - 160.
[4]Synthetic Communications,2011,vol. 41,p. 2835 - 2851.
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 496 - 500.
[6]Chemical Biology and Drug Design,2017,vol. 90,p. 1115 - 1121.
[7]European Journal of Medicinal Chemistry,2019,vol. 168,p. 474 - 490.

22
[ 3473-63-0 ]
[ 4815-24-1 ]
[ 18593-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	In formamide; at 160℃; for 6.0h;Inert atmosphere;	General procedure: A mixture of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (2.6 g, 11.54 mmol) and formamidine acetate (1.20 g, 11.54 mmol) in formamide (4 mL) was heated to 160 oC for 6 h. Within this time period at every 2 h additional formamidine acetate (1.20 g, 11.54 mmol) was added. Water (30 mL) was added and the precipitate that resulted was filtered off, washed with water, and dried in a vacuum oven to give the pyrimidine as a tanned solid (2.3 g, 96%).

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5992 - 5994.

23
[ 18593-44-7 ]
C₈H₉ClN₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; at 90℃; for 3.0h;Inert atmosphere;	General procedure: A solution of 4-hydroxy-5,6,7,8-tetrahydrobenzothieno[2,3-d] pyrimidine (1.0 g, 4.85 mmol) in phosphorous oxychloride (10 mL) was heated to 90 oC for 3 h. Excess phosphorus oxychloride was removed in vacuo and then ice-water (40 mL) was added. The solution was then basified by addition of solid sodium hydrogen carbonate in small portions. The precipitate that resulted was filtered off, washing with water to obtain an off-white solid (1.0 g, 92%)

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5992 - 5994.

24
[ 18593-44-7 ]
[ 4994-89-2 ]