Structure of 106157-82-8
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CAS No. : | 106157-82-8 |
Formula : | C6H7N3O |
M.W : | 137.14 |
SMILES Code : | CC(C1=NC(N)=NC=C1)=O |
MDL No. : | MFCD09263814 |
InChI Key : | XDKSEDDZHXZRKQ-UHFFFAOYSA-N |
Pubchem ID : | 13582270 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 36.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
68.87 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.09 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.13 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.27 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.47 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.16 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.99 |
Solubility | 14.2 mg/ml ; 0.103 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.86 |
Solubility | 18.8 mg/ml ; 0.137 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.6 |
Solubility | 3.45 mg/ml ; 0.0252 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.23 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.51 |
* 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 |
---|---|---|
70% | at 20℃; for 6 h; | A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at r.t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidin-4-yl)ethanone (9.2 g, 70percent). |
70% | at 20℃; for 6 h; | Example 2 1- (2-AMINOPYRIMIDIN-4-YL)-2-BROMOETHANONE hydrobromide The title compound (a) was prepared by working as described in J. Het. Chem. 1985,22, 1723. A mixture of 3,3-dimethoxy-2-butanone (25 9, 189.16 MMOL) and N, N-DIMETHYLFORMAMIDE DIMETHYLACETAL (22.5 g, 189.16 MMOL) were stirred at 110°C for 30 hours and then distilled (115°C, 1 mmHg) thus obtaining 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE, as a yellow solid (27.3 G, 146 mmol, 77percent). Onto a solution of sodium (3.48 g, 151.67 MMOL) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 G, 151.67 MMOL) was added at r. t. , to give a white suspension into which a solution of 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE (28.4 g, 151.67 MMOL) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.56 G). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot and then cooled to yield a second crop. Total amount of 4- (1, 1-DIMETHOXYETHYL) PYRIMIDIN-2-AMINE : 17.66 G, 63. 5percent. A solution of the said amine (17. 5 G, 95.5 MMOL) in formic acid was stirred at r. t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1- (2-aminopyrimidin-4-yl) ethanone (9.2 g, 70percent). To a solution of 1- (2- aminopyrimidin-4-yl) ethanone (412 mg, 3 MMOL) in glacial acetic acid (1 mL) and 48percent aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r. t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 mg, 65percent). |
70% | at 20℃; for 6 h; | A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at r.t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidin-4-yl)ethanone (9.2 g, 70percent). |
70% | at 20℃; for 6 h; | Example 3; 1 -(2-Aminopyrimidin-4-yl)-2-bromoethanone hydrobromi'de; A mixture of 3,3-dimethoxy-2-butanone (25 g, 189.2 mmol) and N1N- dimethylformamide dimethylacetal (22.5 g, 189.2 mmo.) were stirred at 1100C for 30 hours and then distilled (11511C, 1 mmHg) thus obtaining 1-(dimethyiamino)-4,4-dimethoxypent-1-en- 3-oπe, as a yellow solid (27.3 g, 146 mmol, 77percent). Onto a solution of sodium (3.48 g, 151.7 mmol) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 g, 151.7 mmol) was added at r.t. to give a white suspension into which a solution of 1-(dirnethylamino)-4,4- dimethoxypent-1-eπ-3-one (28.4 g, 151.7 mmo.) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.5 g). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot, and then cooled to yield a second crop. The total amount of 4-(1 ,1- dimethoxyethyl)pyrimidin-2-arnine obtained was 17.7 g, 63.5percent, A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at room temperature for 6 hours and concentrated to dryness and the residue was stirred in efhanoi (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidiπ-4-yl)ethanone (9.2 g, 70percent). To a solution of the 1-(2- <n="34"/>aminopyrimidin-4-yl)ethanone (412 mg, 3 mmoi) in glacial acetic acid (1 mL) and 48percent aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r.t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 rng, 65percent).1H NMR (DMSO-d6 / 400 MHz) δ ppm: 4.9 (s, 2 H), 7,0 (d, 2 H), 8.5 (d, 2 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With formic acid; at 20℃; for 6h; | A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at r.t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidin-4-yl)ethanone (9.2 g, 70%). |
70% | With formic acid; at 20℃; for 6h; | Example 2 1- (2-AMINOPYRIMIDIN-4-YL)-2-BROMOETHANONE hydrobromide The title compound (a) was prepared by working as described in J. Het. Chem. 1985,22, 1723. A mixture of 3,3-dimethoxy-2-butanone (25 9, 189.16 MMOL) and N, N-DIMETHYLFORMAMIDE DIMETHYLACETAL (22.5 g, 189.16 MMOL) were stirred at 110C for 30 hours and then distilled (115C, 1 mmHg) thus obtaining 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE, as a yellow solid (27.3 G, 146 mmol, 77%). Onto a solution of sodium (3.48 g, 151.67 MMOL) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 G, 151.67 MMOL) was added at r. t. , to give a white suspension into which a solution of 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE (28.4 g, 151.67 MMOL) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.56 G). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot and then cooled to yield a second crop. Total amount of 4- (1, 1-DIMETHOXYETHYL) PYRIMIDIN-2-AMINE : 17.66 G, 63. 5%. A solution of the said amine (17. 5 G, 95.5 MMOL) in formic acid was stirred at r. t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1- (2-aminopyrimidin-4-yl) ethanone (9.2 g, 70%). To a solution of 1- (2- aminopyrimidin-4-yl) ethanone (412 mg, 3 MMOL) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r. t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 mg, 65%). |
70% | With formic acid; at 20℃; for 6h; | A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at r.t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidin-4-yl)ethanone (9.2 g, 70%). |
70% | With formic acid; at 20℃; for 6h; | Example 3; 1 -(2-Aminopyrimidin-4-yl)-2-bromoethanone hydrobromi'de; A mixture of 3,3-dimethoxy-2-butanone (25 g, 189.2 mmol) and N1N- dimethylformamide dimethylacetal (22.5 g, 189.2 mmo.) were stirred at 1100C for 30 hours and then distilled (11511C, 1 mmHg) thus obtaining 1-(dimethyiamino)-4,4-dimethoxypent-1-en- 3-o?e, as a yellow solid (27.3 g, 146 mmol, 77%). Onto a solution of sodium (3.48 g, 151.7 mmol) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 g, 151.7 mmol) was added at r.t. to give a white suspension into which a solution of 1-(dirnethylamino)-4,4- dimethoxypent-1-e?-3-one (28.4 g, 151.7 mmo.) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.5 g). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot, and then cooled to yield a second crop. The total amount of 4-(1 ,1- dimethoxyethyl)pyrimidin-2-arnine obtained was 17.7 g, 63.5%, A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at room temperature for 6 hours and concentrated to dryness and the residue was stirred in efhanoi (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidi?-4-yl)ethanone (9.2 g, 70%). To a solution of the 1-(2- <n="34"/>aminopyrimidin-4-yl)ethanone (412 mg, 3 mmoi) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r.t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 rng, 65%).1H NMR (DMSO-d6 / 400 MHz) delta ppm: 4.9 (s, 2 H), 7,0 (d, 2 H), 8.5 (d, 2 H) |
With formic acid; at 20℃; for 3h; | Step B: Preparation of [1- (2-AMINO-PYRIMIDIN-4-YL)-ETHANONE] To [4- (1, 1-DIMETHOXY-ETHYL)-PYRIMIDIN-2-YLAMINE] (Step A, 15 g, 81.87 mmol) was added HCOOH (70.0 [ML).] The resulting mixture was stirred at RT under argon for 3 h. The mixture was evaporated to dryness. The solid was [RECRYSTALLIZED] from EtOH to give a brown solid. MS [M/Z] : [138.] 2 (M+H). Calc'd for [C6H8N3O] : 138.14. | |
Compound 3a: 1-(2-aminopyrimidin-4- l)ethanone; To a stirred solution of 4-(1 ,1-dimethoxyethyl)pyrimidin-2-amine (2a) (180 g) in tetrahydrofuran (2 L) was added 2M hydrochloric acid solution (980 mL) and stirring continued at room temperature overnight. Most of the solvent was removed in vacuo and remaining aqueous solution was poured into an aqueous saturated sodium hydrogen carbonate solution. The sandy coloured precipitate was filtered off and dried in vacuo at 40C to give the title compound (1 12 g). In a similar manner were prepared the following: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step C: Preparation of tert-Butyl [7- {2- [L- (2-AMINO-] [PYRIMIDIN-4-YL)-ETHYLAMINO]-BENZOYLAMINO}-4,] 4-dimethyl-3,4- [DIHYDRO-LH-ISOQUINOLINE-2-CARBOXYLATE] To a solution of [1-(2-AMINO-PYRIMIDIN-4-YL)-ETHANONE] (Step B, 200 mg, 1.46 mmol) in toluene (15 mL) was added, 7- [(2-AMINO-BENZOYLAMINO)-4,] 4-dimethyl-3, [4-DIHYDRO-LH-] isoquinoline-2-carboxylic acid tert-butyl ester (Example 15, Step A) (288 mg, 0.73 mmol), and HOAc (3 drops). The resulting mixture was heated at [95 C] under N2 for 20 h. The reaction was cooled to RT and NaBH (OAc) 3 (620 mg, 2.92 mmol) was added and reheated for 3 h. The reaction was cooled to RT, quenched with [NA2CO3] solution (2 M, 5 mL), solvent was evaporated in vacuo. The residue was extracted with CHC13. The organic layer was washed with saturated [NAHC03,] water, brine, dried over [MGS04,] and evaporated in vacuo. The crude solid was purified by chromatography on silica gel. Elution with [CH2CL2 : MEOH] (95: 5) gave THE final compound. MS [M/Z] : 517.3 (M+H). [CALC'D.] for [C2GH37N603-] 517.63. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With water; hydrogen bromide; bromine; In water; at 20℃; for 15h; | To a solution of <strong>[106157-82-8]1-(2-aminopyrimidin-4-yl)ethanone</strong> (412 mg, 3 mmol) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at room temperature for 15 hours. After diluting with ethyl acetate (15 mL), the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 mg, 65%). 1H NMR (DMSO-d6/400 MHz) delta ppm: 4.9 (s, 2 H), 7.0 (d, 2 H), 8.5 (d, 2 H). |
65% | With hydrogen bromide; bromine; acetic acid; In water; at 20℃; for 15h; | Example 2 1- (2-AMINOPYRIMIDIN-4-YL)-2-BROMOETHANONE hydrobromide The title compound (a) was prepared by working as described in J. Het. Chem. 1985,22, 1723. A mixture of 3,3-dimethoxy-2-butanone (25 9, 189.16 MMOL) and N, N-DIMETHYLFORMAMIDE DIMETHYLACETAL (22.5 g, 189.16 MMOL) were stirred at 110C for 30 hours and then distilled (115C, 1 mmHg) thus obtaining 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE, as a yellow solid (27.3 G, 146 mmol, 77%). Onto a solution of sodium (3.48 g, 151.67 MMOL) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 G, 151.67 MMOL) was added at r. t. , to give a white suspension into which a solution of 1-(DIMETHYLAMINO)-4, 4-DIMETHOXYPENT-1-EN-3-ONE (28.4 g, 151.67 MMOL) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.56 G). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot and then cooled to yield a second crop. Total amount of 4- (1, 1-DIMETHOXYETHYL) PYRIMIDIN-2-AMINE : 17.66 G, 63. 5%. A solution of the said amine (17. 5 G, 95.5 MMOL) in formic acid was stirred at r. t. for 6 hours and concentrated to dryness and the residue was stirred in ethanol (50 mL) and then filtered thus obtaining 1- (2-aminopyrimidin-4-yl) ethanone (9.2 g, 70%). To a solution of 1- (2- aminopyrimidin-4-yl) ethanone (412 mg, 3 MMOL) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r. t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 mg, 65%). |
65% | With hydrogen bromide; bromine; acetic acid; In water; at 20℃; for 15h; | To a solution of <strong>[106157-82-8]1-(2-aminopyrimidin-4-yl)ethanone</strong> (412 mg, 3 mmol) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r.t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 mg, 65%). 1H NMR (DMSO-d6/400 MHz) delta ppm: 4.9 (s, 2 H), 7.0 (d, 2 H), 8.5 (d, 2 H). |
65% | With hydrogen bromide; bromine; acetic acid; In water; at 20℃; for 15h; | Example 3; 1 -(2-Aminopyrimidin-4-yl)-2-bromoethanone hydrobromi'de; A mixture of 3,3-dimethoxy-2-butanone (25 g, 189.2 mmol) and N1N- dimethylformamide dimethylacetal (22.5 g, 189.2 mmo.) were stirred at 1100C for 30 hours and then distilled (11511C, 1 mmHg) thus obtaining 1-(dimethyiamino)-4,4-dimethoxypent-1-en- 3-o?e, as a yellow solid (27.3 g, 146 mmol, 77%). Onto a solution of sodium (3.48 g, 151.7 mmol) in anhydrous ethanol (400 mL), solid guanidine hydrochloride (14.5 g, 151.7 mmol) was added at r.t. to give a white suspension into which a solution of 1-(dirnethylamino)-4,4- dimethoxypent-1-e?-3-one (28.4 g, 151.7 mmo.) in anhydrous ethanol (50 mL) was added. The mixture was refluxed for 19 hours. After cooling, the precipitate was filtered and washed with ethanol and with plenty of water, thus obtaining a white solid (8.5 g). The ethanolic solutions were concentrated to dryness, taken up with boiling ethyl acetate (1000 mL), filtered while hot, and then cooled to yield a second crop. The total amount of 4-(1 ,1- dimethoxyethyl)pyrimidin-2-arnine obtained was 17.7 g, 63.5%, A solution of the said amine (17.5 g, 95.5 mmol) in formic acid was stirred at room temperature for 6 hours and concentrated to dryness and the residue was stirred in efhanoi (50 mL) and then filtered thus obtaining 1-(2-aminopyrimidi?-4-yl)ethanone (9.2 g, 70%). To a solution of the 1-(2- <n="34"/>aminopyrimidin-4-yl)ethanone (412 mg, 3 mmoi) in glacial acetic acid (1 mL) and 48% aq. HBr (0.3 mL), bromine (0.153 mL) in acetic acid (0.4 mL) was added and the resulting orange solution was stirred at r.t. for 15 hours. After diluting with ethyl acetate (15 mL) the precipitate was filtered and washed with ethyl acetate thus affording the title compound as a whitish solid (580 rng, 65%).1H NMR (DMSO-d6 / 400 MHz) delta ppm: 4.9 (s, 2 H), 7,0 (d, 2 H), 8.5 (d, 2 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound 5a: 1-(2-aminopyrimidin-4-yl)ethanol; <strong>[106157-82-8]1-(2-aminopyrimidin-4-yl)ethanone</strong> (Compound 3a) (0.5 g) was dissolved in 50 mL methanol and cooled to 0C. Sodium borohydride (0.138 g) was added portion wise and the mixture was stirred for 16 hours at room temperature. Saturated ammonium chloride solution (20 mL) was added and this mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated to give the title compound (270 mg) as a colourless oil that solidified on standing. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; triethylamine;Noyori's catalyst; at 20℃; for 1h;Inert atmosphere; | Compound 6a: (R)-1- 2-aminopyrimidin-4-yl)ethanol; OHTo a solution of <strong>[106157-82-8]1-(2-aminopyrimidin-4-yl)ethanone</strong> (Compound 3a) (59.8 g) in N,N- dimethylformide (600 mL) at room temperature was added chloro[(1 R,2R)-N-(p- toluenesulfonyl)-1 ,2-diphenyl-1 ,2-ethanediamine] (p-cymene)ruthenium (II) (3.35 g). The resulting dark orange solution was then purged with argon and formic acid - triethylamine complex (5:2) (189 g) was added. The reaction was stirred under an atmosphere of argon at room temperature for 1 h then evaporated to dryness under reduced pressure to yield a dark brown residue that was taken up in dichloromethane and the minimal volume of methanol and chromatographed on silica gel eluting with 4- 10% methanol in dichloromethane. Fractions containing product were combined and evaporated under reduced pressure to yield the title compound (29.2 g) that was a 2.4%:97.6% ratio of enantiomers by chiral SFC (supercritical fluid chromatography) chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 20℃; for 1h; | Compound 11a: 1 -(2-aminopyrimidin-4-yl)ethanone oxime; To a suspension of 1 -(2-aminopyrimidin-4-yl)ethanone (3a) (4 g) in ethanol (70 mL) and water (14 mL) was added hydroxylamine hydrochloride (4.05 g) followed by sodium acetate (7.18 g) and the mixture was stirred at room temperature for one hour. After this time the reaction mixture was concentrated in vacuo, water was added and stirred for 15 minutes. The precipitate was collected by filtration and washed with water and dried in vacuo at 40C overnight to afford the title product (4.29 g) as a light yellow solid. |
Tags: 106157-82-8 synthesis path| 106157-82-8 SDS| 106157-82-8 COA| 106157-82-8 purity| 106157-82-8 application| 106157-82-8 NMR| 106157-82-8 COA| 106157-82-8 structure
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