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CAS No. : | 185040-32-8 | MDL No. : | MFCD04115117 |
Formula : | C7H9N3OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WGUCZWYLSKPURM-UHFFFAOYSA-N |
M.W : | 183.23 | Pubchem ID : | 10607520 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.45 |
TPSA : | 80.18 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) : | -6.44 cm/s |
Log Po/w (iLOGP) : | 1.48 |
Log Po/w (XLOGP3) : | 1.38 |
Log Po/w (WLOGP) : | 0.86 |
Log Po/w (MLOGP) : | -0.26 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 0.94 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.02 |
Solubility : | 1.76 mg/ml ; 0.00961 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.67 |
Solubility : | 0.394 mg/ml ; 0.00215 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.54 |
Solubility : | 0.531 mg/ml ; 0.0029 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
81% | With triethylamine; methylamine In tetrahydrofuran | EXAMPLE 16A Alternative synthesis of 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40percent aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81percent) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester; mp 91-93° C. Analysis calculated for C9 H13 N3 O2 S: C, 47.56; H, 5.76; N, 18.49. Found: C, 47.93; H, 5.67; N, 18.58. |
81% | With triethylamine; methylamine In tetrahydrofuran | EXAMPLE 18A Alternative synthesis of 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40percent aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81percent) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester, mp 91°-93° C. Analysis calcd. for C9 H13 N3 O2 S: C, 47.56; H, 5.76; N, 18.49. Found: C, 47.93; H, 5.67; N, 18.58. |
81% | With triethylamine; methylamine In tetrahydrofuran | EXAMPLE 18A Alternative synthesis of 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40percent aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81percent) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester; mp 91°-93° C. Analysis calculated for C9 H13 N3 O2 S: C, 47.56; H, 5.76; N, 18.49. Found: C, 47.93; H, 5.67; N, 18.58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With manganese(IV) oxide In chloroform for 7 h; | In a dry 3 L, three-necked round-bottomed flask fitted with an overhead mechanical stirrer and an argon inlet, 32.74 g (176.7 mmol) of (4-METHYLAMINO-2-METHYLSULFANYL-PYRIMIDIN- 5-yl) -methanol was dissolved in 1.6 L of CHCl3. Manganese dioxide (152 g, 1.75 mol) was added portionwise with stirring. The reaction warmed slightly and was stirred for 7 hours. The manganese dioxide was removed by vacuum filtration through a pad of Celite and was washed well with two 300 mL portions of chloroform. The filtrate was concentrated to find a white solid. After vacuum drying, 30.6 g (94 percent) of 4-methylamino- 2-methylsulfanyl-pyrimidine-5-carbaldehyde was isolated. The spectral data matched literature values. |
92% | With manganese(IV) oxide In chloroform at 20℃; for 3 h; | A mixture of (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (22.0 g, 119 mmol) and MnO2 (44 g, 714 mmol) in CHCl3 (300 mL) was stirred at RT for 3h. The reaction was filtered and the filtrate concentrated to give 4-(methylamino)-2- (methylsulfanyl)pyrimidine-5-carbaldehyde as a pale solid (20 g, 92percent yield). |
92% | With manganese(IV) oxide In chloroform at 20℃; for 3 h; | A mixture of Example Cl (22.0 g, 119 mmol) and MnO2 (44 g, 506 mmol) in CHCl3 (300 mL) was stirred at RT for 3 h. The reaction was filtered and the filtrate was concentrated to give 4-(meylamino)-2-(methylthio)pyrimidme-5-carbaldehyde as a pale solid (20 g, 92percent yield). 1H NMR (400 MHz, OMSO-d6): 9.71 (s, 1 H), 8.60 (br s, 1 H), 8.49 (s, 1 H), 2.96 (d, J = 4.8 Hz, 3H), 2.48 (s, 3 H) MS (ESI) m/z: 184.0 (M+H+). |
91% | With manganese(IV) oxide In dichloromethane at 20℃; for 12 h; | Step 3: Synthesis of 4-(methylamino)-2- (methylthio)pyrimidine-5 -carbaldehydeA suspension of (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (3.1 g, 16.73 mmol) and manganese dioxide (7.27 g, 83.67 mmol) in DCM (40 mL) was stirred at room15 temperature for 12 hours. The resulting precipitate was filtered off, and the filtrate was concentrated to give 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (2.8 g, 91percent) as a yellowish solid. MS (ES+) C7H9N305 requires: 183, found: 184 [M + H]. |
91% | With manganese(IV) oxide In dichloromethane at 20℃; for 12 h; | Step 3: Synthesis of 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde A suspension of (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (3.1 g, 16.73 mmol) and manganese dioxide (7.27 g, 83.67 mmol) in DCM (40 mL) was stirred at room temperature for 12 hours. The resulting precipitate was filtered off, and the filtrate was concentrated to give 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (2.8 g, 91percent) as a yellowish solid. MS (ES+) C7H9N3OS requires: 183, found: 184 [M+H]+. |
91% | With manganese(IV) oxide In dichloromethane at 20℃; for 12 h; | A suspension of (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (3.1 g, 16.73 mmol) and manganese dioxide (7.27 g, 83.67 mmol) in DCM (40 mL) was stirred at room temperature for 12 hours. The resulting precipitate was filtered off, and the filtrate was concentrated to give 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (2.8 g, 91percent) as a yellowish solid. MS (ES+) C7H9N3OS requires: 183, found: 184 [M+H]+. |
89% | With manganese(IV) oxide In dichloromethane at 20℃; | To a solution of (4.4rnethylaniino)-2-(metlwithio)pyrimidimSyl)methanol (210 mg, 1.14 mmol) in dichloromethane (3.8 mL) was added activated Manganesc(1V) oxide (980 mg,11.4 mmoi) at room temperature and stirred for overnight. The reaction mixture was filteredthrough a pad of cehte and concentrated under reduced pressure. The resulting crude product was purified by flash silica gel chromatography with ethyl acetate/hexane (1/9 to 1/4) to give (190 mg, 89percent yield) of the title product as a white solid. 1H NMR 600 MHz (CDCI3) ö 9.67 (s, lii), 8.52 (h lii), 8.27 (s, ILl), 3.10 (d,J 5.4 Hz, 3Ff), 2.54 (s, 3ff). |
89% | With manganese(IV) oxide In dichloromethane at 20℃; for 16 h; | 4- (methylamino) -2- (methylthio) pyrimidine-5-carbaldehyde. A suspension of compound 3 (18.3 g, 0.1 mol) and MnO2(86.9 g, 1 mol) in DCM (1 L) was stirred at room temperature for 16 h. TLC indicated that compound 3 was completely consumed. The reaction mixture was filtered through a pad of celite. The cake was washed with EA (50 mL) . The filtrate and wash were combined and concentrated under reduced pressure to obtain 18.3 g of the desired product as a white solid. Yield: 89percent |
80% | With manganese(IV) oxide In dichloromethane for 24 h; | To a solution of 4-methylamino-2-methylthiopyrimidine-5-methanol (20 g, 108 mmol) in 1 L of dichloromethane was added 87 g (1 mol) of manganese dioxide. The resulting suspension was stirred for 24 hours and then filtered through a filter aid. The filter residue was washed with 100 mL of dichloromethane and the combined filtrate and washings were evaporated under reduced pressure to give 15.8 g (80percent) of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde as a white solid. |
76% | With manganese(IV) oxide In dichloromethane at 20℃; for 12 h; | Step 3. MnO2 (13.0 g, 151.1 mmol, 7.0 eq.) was added to a solution of 4-(methylamino)-2-(methylthio)-pyrimidin-5-yl)-methanol (4.0 g, 21.6 mmol, 1.0 eq) in CH2Cl2 (200 mL). The resulted mixture was stirred for 12 h at room temperature, filtered and concentrated to afford 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (3.0 g, 76percent in yield). |
75% | With manganese(IV) oxide In dichloromethane for 24 h; | Step 4: Intermediate 6 [00721j Compound 5 (4.23 g, 23.2 mmol) was taken into dichloromethane (1 L) and treated with manganese dioxide (18.0 g, 207 mmol) with stirring. The resultant suspension was stirred for 24 h, then filtered through Celite, washed with dichloromethane (100 mL), and the combined organic layers were concentrated to afford the title compound (3.00 g, 75percent). |
80% | With manganese dioxide In dichloromethane | Step 1.3 Preparation of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde 4-Methylamino-2-methylthiopyrimidine-5-methanol (20 g, 108 mmol) and 1 L of dichloromethane were combined with stirring and treated with 87 g (1 mol) of manganese dioxide. The resulting suspension was stirred for 24 hours and then filtered through a filter aid. The filter residue was washed with 100 mL of dichloromethane and the combined filtrate and washings were evaporated under reduced pressure to give 15.8 g (80percent) of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde as a white solid. |
80% | With manganese dioxide In dichloromethane | 4-Methylamino-2-methylthiopyrimidine-5-methanol (20 g, 108 mmol) and 1 L of dichloromethane were combined with stirring and treated with manganese dioxide (87 g, 1 mol). The resulting suspension was stirred for 24 hours and then filtered through a filter aid. The filter residue was washed with 100 mL of dichloromethane and the combined filtrate and washings were evaporated under reduced pressure to give 15.8 g (80percent) of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde as a white solid. |
80% | With manganese dioxide In dichloromethane | c) 20 g (108 mmol) of 4-methylamino-2-methylthiopyrimidine-5-methanol were stirred in 1 l of dichloromethane and treated with 87 g (1 mol) of manganese dioxide. The resulting suspension was stirred for 24 hours and then filtered through a filter aid. The filter residue was washed with 100 ml of dichloromethane and the combined filtrate and washings were evaporated under reduced pressure to give 15.8 g (80percent) of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine; methylamine In tetrahydrofuran | EXAMPLE 16A Alternative synthesis of 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40percent aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81percent) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester; mp 91-93° C. Analysis calculated for C9 H13 N3 O2 S: C, 47.56; H, 5.76; N, 18.49. Found: C, 47.93; H, 5.67; N, 18.58. |
81% | With triethylamine; methylamine In tetrahydrofuran | EXAMPLE 18A Alternative synthesis of 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40percent aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81percent) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester, mp 91°-93° C. Analysis calcd. for C9 H13 N3 O2 S: C, 47.56; H, 5.76; N, 18.49. Found: C, 47.93; H, 5.67; N, 18.58. |
81% | With triethylamine; methylamine In tetrahydrofuran | EXAMPLE 18A Alternative synthesis of 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40percent aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81percent) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester; mp 91°-93° C. Analysis calculated for C9 H13 N3 O2 S: C, 47.56; H, 5.76; N, 18.49. Found: C, 47.93; H, 5.67; N, 18.58. |
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