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CAS No. : | 588-36-3 | MDL No. : | MFCD08236793 |
Formula : | C6H9N3OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLVOWGDFXAVSFE-UHFFFAOYSA-N |
M.W : | 171.22 | Pubchem ID : | 220531 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 44.29 |
TPSA : | 97.33 Ų |
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) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 1.4 |
Log Po/w (XLOGP3) : | 0.37 |
Log Po/w (WLOGP) : | 0.13 |
Log Po/w (MLOGP) : | -0.92 |
Log Po/w (SILICOS-IT) : | 0.56 |
Consensus Log Po/w : | 0.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.41 |
Solubility : | 6.72 mg/ml ; 0.0392 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.98 |
Solubility : | 1.8 mg/ml ; 0.0105 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.62 |
Solubility : | 4.15 mg/ml ; 0.0242 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With manganese(IV) oxide In chloroform at 55℃; for 4 h; | Method A: Add Mn02 (49.8 g, 572 mmol) to a suspension of 4-amino-2-(methylthio)pyrimidin- 5-yl)methanol (28 g, 164 mmol) in chloroform (818 mL) and heat the reaction at 55 °C (measure internally) for 4 h. Filter the hot reaction mixture and rinse the filter cake with hot chloroform and THF. Concentrate the combined filtrates under reduced pressure and dry under vacuum to afford the title compound (26.7 g, 96percent yield) as a pale yellow solid MS (m/z): 170.1(M+1). |
94% | With manganese(IV) oxide In chloroform at 20℃; | To a solution of (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (11 g, 63 mmol, 1.0 equiv) in CHC13 (900 mL) was added Mn02 (43.85 g, 504 mmol, 8.0 equiv). The suspension was stirred overnight at rt. The resulting mixture was filtration and washing with CHC13. The filtrate was concentrated under vacuum to give 10 g (94percent) of 4-amino-2- (methylthio)pyrimidine-5 -carbaldehyde as a white solid. |
94% | With manganese(IV) oxide In chloroform at 20℃; | To a solution of (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (11 g, 63 mmol, 1.0 equiv) in CHC13 (900 mL) was added Mn02 (43.85 g, 504 mmol, 8.0 equiv). The suspension was stirred overnight at rt. The resulting mixture was filtration and washing with CHCI3. The filtrate was concentrated under vacuum to give 10 g (94percent) of 4-amino-2-(methylthio)pyrimidine-5- carbaldehyde as a white solid. |
72% | With manganese(IV) oxide In chloroform at 20℃; | General procedure: The compound (3) (1 equiv.) was dissolved in chloroform to which Mn02 (6 equiv.) wasadded. The resulting suspension was stirred overnight, an additional portion of Mn02 (1.5 equiv.)was added and stirring was continued for a further 12 h. The solids were removed by filtration through a diatomaceous earth pad, which was washed with further chloroform. The chloroform was evaporated in vacuum to obtain the product (4).Starting from compound (3a), compound (4a) was obtained in 72percent yield using themethod described in General Procedure C. ‘H NMR (300 MHz, DMSO-d6), ö 2.55 (s, S-CH3, 3H), 5.74 (bs, NH, 1H), 8.20 (bs, NH, 1H), 8.45 (s, Ar-H, 1H), 9.80 (s, HC=O, 1H). |
52% | With manganese(IV) oxide In dichloromethane at 18 - 25℃; | Step 2: Intermediate 2 [00830j A mixture of Intermediate 1 (7.5 g, 44 mmol) and Mn02 (55 g, 630 mmol) in DCM (60 mL) was allowed to stir at room temperature overnight. The mixture was filtered, and the filtrate was concentrated. The resultant residue was purified by colunm chromatography (DCM:MeOH=20: 1) to afford the title compound as light yellow solid (3.85 g, 52percent). LCMS:170.2 [M+1]. ‘H NMR (400 MHz, CDC13): ö 2.55 (s, 3H), 8.42 (s, 1H), 9.78 (s, 1H). |
51.6% | With manganese(IV) oxide In tetrahydrofuran at 40 - 45℃; for 16 h; | step 3: To a 3 L three-necked flask was added (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (100 g, 0.58 mol), activated MnO2 (152 g, 1.75 mol) and THF (2000 mL). The mixture was heated to 40-45° C. for 16 h. The reaction mixture was cooled to 20-25° C., filtered through a CELITE pad, and rinsed with THF (400 mL×3). The combined filtrates were concentrated to dryness. Pure 4-amino-2-(methylthio)pyrimidine-5-carbaldehyde (51 g, 51.6percent) was obtained by trituration in 200 mL EtOAc/n-heptane (1:5) at 20-25° C., followed by removal of the solvent in vacuo; 1H-NMR (CDCl3, 400 MHz) δ 9.80 (s, 1H), 8.44 (s, 1H), 8.22 (br, 1H), 5.77 (br, 1H), 2.57 (s, 3H); LC/MS: m/z=169.8 [M+H]+. |
73% | With manganese dioxide In dichloromethane | c) 28 g (164 mmol) of 4-amino-2-methylthiopyrimidine-5-methanol were stirred in 500 ml of dichloromethane and treated with 150 g (1.7 mol) of manganese dioxide. The suspension was stirred for 24 hours and then filtered through a filter aid. The filtrate was evaporated to give 20.2 g (73percent) of 4-amino-2-methylthiopyrimidine 5-carboxaldehyde as a pale yellow solid. |
10 g | With manganese(IV) oxide In chloroform at 20℃; | To a solution of (4-amino-2-(methylthio)pyrimidin-5 -yl)methanol (11 g, 63 mmol, 1.0 equiv) in CHC13 (900 mL) was added Mn02 (43.85 g, 504 mmol, 8.0 equiv). The suspension was stirred overnight at rt. The resulting mixture was filtration and washing with CHC13. The filtrate was concentrated under vacuum to give 10 g (94percent) of 4-amino-2-(methylthio)pyrimidine-5- carbaldehyde as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Stage #2: With water; potassium hydroxide In tetrahydrofuran at 0℃; for 1 h; |
Cool a solution of ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate (72.3 g, 339 mmol) in tetrahydrofuran (THF) (900 mL) to 0°C. Add a solution of LiAlH4 (2 M in THF) (195 mL, 390 mmol) dropwise over 1 h. Stir for 2 h at 0°C and allow the reaction to warm to RT overnight. Cool the mixture to 0°C and cautiously quench by the sequential addition of water (15 mL), 20percent aq. KOH (15 mL) and water (30 mL). Stir the resulting mixture for 1 h. Dry over MgS04, filter, concentrate under reduced pressure, and dry under vacuum to obtain the title compound (55.85 g, 96percent yield). MS (m/z): 172.1(M+1). |
95% | With lithium aluminium tetrahydride In tetrahydrofuran at -20 - 20℃; for 5 h; Inert atmosphere | General procedure: Lithium aluminum hydride (1.5 equiv.) was suspended in THF under a nitrogen atmosphere, and the mixture was cooled with dry ice. The compound (2) (1 equiv.) wasdissolved in THF and added dropwise to the cooled solution while keeping the reaction temperature below -20 °C. The reaction mixture was allowed to warm to room temperature, and stirred for 5 h. The reaction was then quenched by the addition of water (5 mL), 15percent NaOH (10 mL) and then further water (15 mL). The white solid that precipitated was filtered and the filtrate was evaporated under reduced pressure to obtain the product as a yellow solid.(3a)Starting from compound (2a), 95percent of compound (3a)was obtained in 95percent yield usingthe method described in General Procedure B. ‘H NMR (300 MHz, DMSO-d6), ö 2.56 (s, S-CH3,3H), 4.25 (s, CH2OH, 2H), 5.30 (br s, OH, 1H), 6.70 (br s, NH2, 2H), 7.85 (s, Ar-H, 1H). |
76% | With sodium hydroxide In tetrahydrofuran; hexane; water; ethyl acetate | Example 12 (4-Amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol A solution of 4-amino-2-methanesulfanyl-pyrimidine-5-carboxylic acid ethyl ester (13.36 g, 63 mmol) in 250 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (3.82 g, 100 mmol) in 250 mL of tetrahydrofuran. After 30 minutes, the reaction was cooled to 0° C., and isopropyl alcohol was added until bubbling diminished. The reaction was quenched with 15 mL of water, 15 mL of 15percent NaOH, and 50 mL of water, and the mixture was stirred for 1 hour. The white precipitate was removed by filtration, washing with ethyl acetate. The filtrate was concentrated in vacuo and 3:1 hexane:ethyl acetate was added. The solids were collected, washed with 3:1 hexane:ethyl acetate, followed by hexane. The solid was dissolved in ethyl acetate, and the solution was dried over magnesium sulfate. Filtration followed by concentration in vacuo gave 8.14 g (76percent) of (4-amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol. Analysis calculated for C6H9N3OS: C, 42.09; H, 5.30; N, 24.54. Found: C, 42.31; H, 5.24; N, 24.27. |
76% | With sodium hydroxide In tetrahydrofuran; hexane; water; ethyl acetate | Example 12 (4-Amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol A solution of 4-amino-2-methanesulfanyl-pyrimidine-5-carboxylic acid ethyl ester (13.36 g, 63 mmol) in 250 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (3.82 g, 100 mmol) in 250 mL of tetrahydrofuran. After 30 minutes, the reaction was cooled to 0° C., and isopropyl alcohol was added until bubbling diminished. The reaction was quenched with 15 mL of water, 15 mL of 15percent NaOH, and 50 mL of water, and the mixture was stirred for 1 hour. The white precipitate was removed by filtration, washing with ethyl acetate. The filtrate was concentrated in vacuo and 3:1 hexane:ethyl acetate was added. The solids were collected, washed with 3:1 hexane:ethyl acetate, followed by hexane. The solid was dissolved in ethyl acetate, and the solution was dried over magnesium sulfate. Filtration followed by concentration in vacuo gave 8.14 g (76percent) of (4-amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol. Analysis calculated for C6H9N3OS: C, 42.09; H, 5.30; N, 24.54. Found: C, 42.31; H, 5.24; N, 24.27. |
7.55 g | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 1 h; | Step 1: Intermediate 1 [00829j To a solution of(9.0 g, 42 mmol) in anhydrous THF (50 mL) was added LiA1H4 (3.2 g, 84 mmol) in portions at 0 °C after which the mixture was stirred at room temperature for 1 h. Na2SO4-10H20 was added to the mixture followed by filtration. The filtrate was concentrated to afford the title compound as a yellow solid (7.55 g). LCMS: 172.3 [M+1]. ‘H NMR (400 MHz, CDC13): ö 1.38 (dd, 3H), 2.52 (s, 3H), 4.34 (q, 2H), 5.62-5.49 (m, 1H), 8.70 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydroxide In tetrahydrofuran; diethyl ether; water; ethyl acetate | Step 2.2 Preparation of4-amino-2-methylthiopyrimidine-5-methanol To a 0° C. solution of lithium aluminum hydride (175 mL, 175 mmol) in diethyl ether was added dropwise a solution of 4-amino-2-methylthiopyrimidine-5-carboxylate (34.7 g, 163 mmol) in 500 mL of dry tetrahydrofuran over a period of 1.5 hours. The reaction mixture was slowly warmed to ambient temperature and then cooled back to 0° C. before carefully quenching with 7 mL of water, 7 mL of 2 M sodium hydroxide solution, followed by 14 mL of water. The resulting suspension was filtered and the residue was washed with 2*300 mL of ethyl acetate. The filtrates were combined and concentrated to give 23.0 g (83percent) of 4-amino-2-methylthiopyrimidine-5-methanol as a white solid. |
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