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[ CAS No. 148550-51-0 ] {[proInfo.proName]}

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Chemical Structure| 148550-51-0
Chemical Structure| 148550-51-0
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Product Details of [ 148550-51-0 ]

CAS No. :148550-51-0 MDL No. :MFCD07366751
Formula : C8H10N2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :SHVJIPVRIOSGCA-UHFFFAOYSA-N
M.W : 230.24 Pubchem ID :254889
Synonyms :

Calculated chemistry of [ 148550-51-0 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.21
TPSA : 94.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : -0.01
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : -0.51
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.29
Solubility : 11.7 mg/ml ; 0.0509 mol/l
Class : Very soluble
Log S (Ali) : -1.53
Solubility : 6.84 mg/ml ; 0.0297 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.809 mg/ml ; 0.00352 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 148550-51-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 148550-51-0 ]

* 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.

  • Upstream synthesis route of [ 148550-51-0 ]
  • Downstream synthetic route of [ 148550-51-0 ]

[ 148550-51-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 148550-51-0 ]
  • [ 57401-76-0 ]
YieldReaction ConditionsOperation in experiment
76% With ammonium hydroxide In acetonitrile at 20℃; Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (2.15 g, 9.34 mmol) was dissolved in acetonitrile (11.7 ml), and, with stirring at room temperature, aqueous 32percent ammonium hydroxide (11.36 ml, 93 mmol) was added drop wise. A white suspension was obtained after few seconds. Acetonitrile was evaporated and the aqueous suspension was filtered on a buckner funnel. The obtained solid was washed with water (20 ml) and dried affording ethyl 2-aminopyrimidine-5-carboxylate as a white solid (1.192 g, 7.13 mmol, 76percent yield, MS/ESI+ 168.1 [MH]+).
76% With ammonium hydroxide In water; acetonitrile at 20℃; Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (2.15 g, 9.34 mmol) was dissolved in acetonitrile (1 1.7 ml) and, stirring at room temperature, aqueous 32percent ammonium hydroxide (1 1.36 ml, 93 mmol) was added drop wise. A white suspension was obtained after few seconds. Acetonitrile was evaporated and the aqueous suspension was filtered on a buckner funnel. The obtained solid was washed with water (20 ml) and dried affording ethyl 2-aminopyrimidine-5- carboxylate as a white solid (1.192 g, 7.13 mmol, 76percent yield, MS/ESI+ 168.1 [MH] +).
Reference: [1] Patent: US2013/79313, 2013, A1, . Location in patent: Paragraph 1024
[2] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 276
  • 2
  • [ 73781-88-1 ]
  • [ 148550-51-0 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1.66667 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
Step 2: Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (121); [0725] A solution of sulfide 120 (0.424 g, 2.14 mmol) in DCM (9 rnL) was treated with a solution of 3-chloroperoxybenzoic acid (mCPBA) (2.0 g) in DCM (9 rnL) then the reaction mixture was stirred at room temperature for 100 min, quenched with a solution OfNa2S2O3 inH2O, diluted with DCM and washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to give compound 121 (0.374 g, 76percent yield).[0726] MS: 230.1 (calc) 230.9 (obs)
76% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 0.5 h; 0 ° C conditions,M-CPBA (458 mg, 2.65 mmol)In CH2Cl2 (18 mL) was added dropwise to a solution of compound 12 (210 mg, 1.06 mmol)In CH2Cl2 (18 mL)Stirring at room temperature for 30 minutes,The reaction solution was allowed to stand at room temperature for 6 hours,Followed by saturated NaHSO3 (18 mL),Saturated NaHCO3 (3 x 18 mL) and saturated brine (18 mL)Na2SO4 dried,The product was thawed under reduced pressure. Yield 76percent
75% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1 h; Step B: Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylateEthyl 2-(methylthio)pyrimidine-5-carboxylate (2.2 g, 11 mmol) was dissolved in DCM at 0 °C and stirred at room temperature for 15 minutes, followed by addition of /w-chloroperbenzoic acid (mCPBA) (5.75 g, 33 mmol). The reaction mixture was stirred for 1 hour. Saturated NaHC03 solution was added to reaction mass and extracted with DCM. The organic layer was washed with water, brine solution and dried oyer an anhydrous Na2S04. The solvent was evaporated to get the title compound (2.0 g, Yield 75 percent).
67% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3 h; Step 2: Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (149)A suspension of mCPBA (5.47 g, 31.68 mmol) in dichloromethane (30 ml) was added to a solution of 148 (1.57 g, 7.92 mmol) in dichloromethane (20 ml) at 0° C. The reaction mixture was allowed to warm to room temperature, stirred for an additional 3 h and quenched with an aqueous solution of Na2S2O3. The mixture was extracted with dichloromethane and the extract was washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo. The solid residue was purified by flash chromatography (eluent 0.5-1percent MeOH/dichloromethane) to afford the title compound 149 as a white solid (1.23 g, 67percent yield). 1H NMR: (DMSO) δ (ppm): 9.48 (s, 2H), 4.42 (q, J=7.1 Hz, 2H), 3.47 (s, 3H), 1.36 (t, J=7.0 Hz, 3H). LRMS (ESI): (calc.) 230.0; (obt.) 231.0 (M+H)+.
66% With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃; for 2.5 h; Stage 2 - Sulfide oxidation to yield ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (Intermediate F); To a stirred solution of stage 1 product (13g, 47.59mmol) in dry THF (25OmL) was slowly added over 30 minutes a solution of mCPBA (47.59g, 275.76mmol) in THF (15OmL) at O0C under N2. The reaction mixture was allowed to warm to RT and stirred for 2h. The reaction mixture was then concentrated in vacuo to about 10OmL and the product / benzoic acid mixture pre-absorbed onto silica gel. Purification was achieved via column chromatography (neat hexane initially, then 1 :5:3 CH2Cl2/heptane/Et20, followed by 1 :1 :1 CH2CI2/heptane/Et2O). The desired compound was obtained as a white solid (10g, 66percent). m/z = 231 [M+H]+, 1H NMR (300MHz1 c/6-DMSO) δ: 1.40 (3H, t), 3.50 (3H, s), 4.40 (2H1 q), 9.50 (2H, s).
66% With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃; for 2.5 h; To a stirred solution of ethyl 2-(methylthio)pyrimidine-5-carboxylate (13g, 47.59mmol) in dry THF (250ml) was slowly added over 30 min a solution of mCPBA (47.59g, 275.76mmol) in THF (150ml) at O0C under N2. The reaction mixture was allowed to warm to r.t. and stirred for 2 h. The reaction mixture was then concentrated in vacuo to about 100ml and the product / benzoic acid mixture pre-absorbed onto silica gel. Purification was achieved via chromatography, eluting with neat hexane initially, then 1 :5:3 CH2CI2/heptane/Et2ψ, followed by 1 :1 :1 CH2CI2/heptane/Et20. The title compound was obtained as a white solid (10g, 66percent). m/z 231 [M+H]+, 1H NMR (300 MHz, CZ6-DMSO) δ: 1.40 (3H, t), 3.50 (3H, s), 4.40 (2H, q), 9.50 (2H, s).
52% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 3 h; Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate
To a stirred solution of ethyl 2-(methylsulfanyl)pyrimidine-5-carboxylate (3.3 g, 16.6 mmol) in DCM (30 mL), m-CPBA (11.49 g, 66.5 mmol) in DCM (30 mL) was added drop wise.
The reaction mixture was stirred at RT for 3 h.
The reaction mixture was quenched with water and extracted with ethyl acetate, washed with saturated NaHCO3 solution, water and brine.
The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to obtain the product as off white solid.
This has been taken as such for the next step (2.0 g, yield: 52.0percent); 1H NMR (300 MHz, DMSO-d6): δ 9.48 (s, 2H), 4.39-4.46 (q, 2H), 3.48 (s, 3H), 1.33-1.39 (t, 3H).
50.7% With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃; for 3 h; To a stirred solution of ethyl 2-(methylthio)pyrimidine-5-carboxylate (2.8 g, 14.2 mmol) in tetrahydrofuran at 0 °C, 3-chloroperbenzoic acid (7.8 g, 60.7mmol, spectrochem) was added and the resulting solution was stirred at rt for 3 h. It was concentrated. DCM was added and was washed with water (25 mL) and 10percent sodium bicarbonate solution (20 mL) and dried over Na2SO4. After evaporation of the solvents, the crude product was purified by flash chromatography to afford the titled product. Yield: 50.7 percent (1 .65 g, off white solid).1H NMR (400 MHz, DMSO-d6): 9.48 (s, 2H), 4.43 (q, J = 7.0 Hz, 2H), 3.48 (s, 3H), 1.37 (t, J = 7.1 Hz, 3H), LCMS: (Method A) 230.9 (M+H), Rt. 2.33 min, 97.48percent (Max).
50.7% With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃; for 3 h; To a stirred solution of ethyl 2-(methylthio)pyrimidine-5-carboxylate (2.8 g, 14.2 mmol) in tetrahydrofuran at 0 °C 3-chloroperbenzoic acid (7.8 g, 60.7mmol, spectrochem) was added and the resulting solution was stirred at rt for 3 h. It was concentrated. DCM was added and was washed with water (25 mL) and 10percent sodium bicarbonate solution (20 mL) and dried over Na2SO4. After evaporation of the solvents, the crude product was purified by flash chromatography to afford the titled product. Yield: 50.7 percent (1.65 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 9.48 (s, 2H), 4.43 (q, J = 7.0 Hz, 2H), 3.48 (s, 3H), 1.37 (t, J = 7.1 Hz, 3H), LCMS: (Method A) 230.9 (M+H),Rt. 2.33 min, 97.48percent (Max).
1.65 g With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃; for 3 h; To a stirred solution of ethyl 2-(methylthio)pyrimidine-5-carboxylate (2.8 g, 14.2 mmol)in tetrahydrofuran at 0 °C, 3-chloroperbenzoic acid (7.8 g, 60.7mmol, spectrochem)was added and the resulting solution was stirred at rt for 3 h. It was concentrated. DCM was added and was washed with water (25 mL) and 10percent sodium bicarbonate solution (20 mL) and dried over Na2SO4. After evaporation of the solvents, the crude product was purified by flash chromatography to afford the titled product. Yield: 50.7 percent (1 .65 g,off white solid).1H NMR (400 MHz, DMSO-d6): 9.48 (s, 2H), 4.43 (q, J = 7.0 Hz, 2H),3.48 (s, 3H), 1.37 (t, J= 7.1 Hz, 3H), LCMS: (Method A) 230.9 (M+H), Rt. 2.33 mm,97.48percent (Max).

Reference: [1] Synthetic Communications, 1993, vol. 23, # 6, p. 715 - 723
[2] Patent: WO2007/118137, 2007, A1, . Location in patent: Page/Page column 105
[3] Chemical Biology and Drug Design, 2016, vol. 87, # 3, p. 472 - 477
[4] Patent: CN106279044, 2017, A, . Location in patent: Paragraph 0026; 0030; 0070; 0071
[5] Patent: WO2012/117421, 2012, A1, . Location in patent: Page/Page column 44
[6] Patent: US2008/227826, 2008, A1, . Location in patent: Page/Page column 27-28
[7] Patent: WO2008/53131, 2008, A1, . Location in patent: Page/Page column 35
[8] Patent: WO2006/123121, 2006, A1, . Location in patent: Page/Page column 17; 26-27
[9] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8663 - 8678
[10] Patent: US2016/333004, 2016, A1, . Location in patent: Paragraph 0386
[11] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 155
[12] Patent: WO2017/144635, 2017, A1, . Location in patent: Page/Page column 51; 52
[13] Patent: US2009/105264, 2009, A1, . Location in patent: Page/Page column 33
[14] Patent: WO2007/55942, 2007, A2, . Location in patent: Page/Page column 63-65
[15] Patent: WO2017/144637, 2017, A1, . Location in patent: Page/Page column 87
  • 3
  • [ 5909-24-0 ]
  • [ 148550-51-0 ]
YieldReaction ConditionsOperation in experiment
2.154 g
Stage #1: With acetic acid; zinc In tetrahydrofuranReflux
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;
Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (10 g, 43.0 mmol) was suspended in dry THF (50 ml), and zinc powder (8.43 g, 129 mmol) was carefully added. The suspension was heated to reflux in a previously heated bath, and then acetic acid (2.460 ml, 43.0 mmol) was added drop wise. The mixture was reacted at the same temperature overnight. The suspension was filtered through a celite pad washing with DCM and MeOH; the filtrate was evaporated and the residue was triturated with DCM:Et2O=1:1. The precipitate was discarded and the solution evaporated and purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=9:1). After solvent evaporation, the residue was treated with diethyl ether and the precipitate was filtered off. The filtrate was evaporated to dryness affording a mixture of ethyl 2-(methylthio)pyrimidine-5-carboxylate and ethyl 2,4-bis(methylthio)pyrimidine-5-carboxylate (about 1:1 ratio) as a colorless oil (3.47 g, MS/ESI+ 199.1 [MH]+; MS/ESI+ 245.0 [MH]+) A mixture of ethyl 2-(methylthio)pyrimidine-5-carboxylate and ethyl 2,4-bis(methylthio)pyrimidine-5-carboxylate (about 1:1 ratio; 3.47 g) was dissolved in DCM (78 ml), and m-CPBA (77percent w/w; 10.54 g, 47.0 mmol) was added portion wise stirring at room temperature. The reaction was stirred at the same temperature overnight. The obtained suspension was filtered washing with DCM and the filtrate was evaporated. The crude was dissolved in ethyl acetate (250 ml) and washed twice with a sat. NaHCO3 (100 ml×2); the organic phase was dried over sodium sulfate and evaporated. The crude was purified by flash chromatography on silica gel column (DCM:iPr2O=3:7) affording ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate as an off-white solid (2.154 g, 9.31 mmol, 21.7percent yield over two steps, MS/ESI+ 231.0 [MH]+). This intermediate proved to be instable on air and it must be kept under vacuum
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8663 - 8678
[2] Patent: WO2012/117421, 2012, A1,
[3] Patent: US2013/79313, 2013, A1, . Location in patent: Paragraph 1022; 1023
[4] Chemical Biology and Drug Design, 2016, vol. 87, # 3, p. 472 - 477
[5] Patent: WO2016/30443, 2016, A1,
[6] Patent: US2016/333004, 2016, A1,
[7] Patent: CN106279044, 2017, A,
[8] Patent: WO2017/144637, 2017, A1,
[9] Patent: WO2017/144635, 2017, A1,
[10] Patent: WO2013/45280, 2013, A1,
  • 4
  • [ 5909-25-1 ]
  • [ 73781-88-1 ]
  • [ 148550-51-0 ]
YieldReaction ConditionsOperation in experiment
21.7% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; A mixture of ethyl 2-(methylthio)pyrimidine-5-carboxylate and ethyl 2,4-bis(methylthio)pyrimidine-5-carboxylate (about 1 : 1 ratio; 3.47 g) was dissolved in DCM (78 ml) and m-CPBA (77percent w/w; 10.54 g, 47.0 mmol) was added portion wise stirring at room temperature. The reaction was stirred at the same temperature overnight. The obtained suspension was filtered washing with DCM and the filtrate was evaporated. The crude was dissolved in ethyl acetate (250 ml) and washed twice with a sat. NaHC03 (100 ml x 2); the organic phase was dried over sodium sulfate and evaporated. The crude was purified by flash chromatography on silica gel column (DCM : iPr20 = 3 : 7) affording ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate as an off-white solid (2.154 g, 9.31 mmol, 21.7percent yield over two steps, MS/ESI+ 231.0 [MH] +). This intermediate proved to be instable on air and it must be kept under vacuum.
Reference: [1] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 275; 276
  • 5
  • [ 6457-49-4 ]
  • [ 148550-51-0 ]
  • [ 875318-46-0 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667 h;
Stage #2: for 0.333333 h;
Stage 1 - Coupling; Piperidin-4yl-methanol (2.48g, 21.55mmol) was stirred in 1 :1 DMF/MeCN (2OmL) with K2CO3 (8.9g, 64.65mmol) for 10 minutes at RT under a nitrogen atmosphere. Intermediate F (5g, 21.55mmol) was then added and the reaction allowed to stir for 20 minutes. It was then diluted with H2O (10OmL) and extracted with EtOAc (2 x 10OmL). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give the product as an orange solid which was used in the next step without further purification (5.7Og, 99percent). m/z = 266 [M+H]+.
54% With potassium carbonate In acetonitrile at 10 - 20℃; for 4 h; A solution of 2-(methylsulfonyl)- 5-pyrimidinecarboxylic acid, ethyl ester (0.094 mol)in acetonitrile (40ml) was added at 10°C to a suspension of 4-piperidinemethanol(0.086 mol) and potassium carbonate (0.172 mol) in acetonitrile (200ml) under N2flow. The mixture was brought to room temperature, then stirred for 4 hours, pouredout into water and extracted with EtOAc. The organic layer was separated, dried(MgSO4), filtered, and the solvent was evaporated. The residue (23 g) was crystallizedfrom acetonitrile/diethyl ether. The precipitate was filtered off and dried, yielding 7.8g(34percent) of intermediate 8. The mother layer was evaporated. The residue (17g) waspurified by column chromatography over silica gel (20-45um) (eluent:DCM/MeOH/NH4OH 97/3/0.1). The pure fractions were collected and the solvent wasevaporated, yielding 4.6g (20percent) of intermediate 8, melting point 129°C.
20% With potassium carbonate In acetonitrile at 10 - 20℃; for 4 h; a) Preparation of intermediate 3 A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid ethyl ester (0.094 mol) in acetonitrile (40ml) was added at 1O0C to a suspension of 4-piperidinemethanol (0.086 mol) and K2CO3 (0.172 mol) in acetonitrile (200ml) under N2 flow. The mixture was brought to room temperature, then stirred for 4 hours, poured into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (23 g) was crystallized from acetonitrile/diethyl ether. The mother layer was evaporated and the obtained residue was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 97/3/0.1; 20-45μm). The pure fractions were collected and the solvent was evaporated, yielding 4.6g (20percent) (M.P.: 129°C) of intermediate 3.
20% With potassium carbonate In acetonitrile at 10 - 20℃; for 4 h; a) Preparation of intermediate 7 A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.094 mol) in acetonitrile (40ml) was added at 100C to a suspension of 4-piperidinemethanol (0.086 mol) and potassium carbonate (0.172 mol) in acetonitrile (200ml) under N2 flow. The mixture was brought to room temperature, then stirred for 4 hours, poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (23g) was crystallized from CHβCN/diethyl ether. The precipitate was filtered off and dried, yielding 7.8g (34percent) of intermediate 7. The residue was purified by column chromatography over silica gel (20-45 μm) (eluent: DCM/MeOH/NH4OH 97/3/0.1). The pure fractions were collected and the solvent was evaporated, yielding 4.6g (20percent) of intermediate 7, melting point 129°C.

Reference: [1] Patent: WO2008/53131, 2008, A1, . Location in patent: Page/Page column 51; 53
[2] Patent: WO2006/10750, 2006, A1, . Location in patent: Page/Page column 30-31
[3] Patent: WO2007/82878, 2007, A1, . Location in patent: Page/Page column 26
[4] Patent: WO2007/82882, 2007, A1, . Location in patent: Page/Page column 30
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