Alternatived Products of [ 16858-56-3 ]
Product Details of [ 16858-56-3 ]
CAS No. : | 16858-56-3 |
MDL No. : | MFCD09878518 |
Formula : |
C6H4ClN3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | SDYFYBAYSDNFRP-UHFFFAOYSA-N |
M.W : |
153.57
|
Pubchem ID : | 12355082 |
Synonyms : |
|
Application In Synthesis of [ 16858-56-3 ]
* 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 [ 16858-56-3 ]
- Downstream synthetic route of [ 16858-56-3 ]
- 1
-
[ 4637-24-5 ]
-
[ 16858-56-3 ]
-
[ 83256-19-3 ]
- 4
-
[ 5424-21-5 ]
-
32-2-Chloro-4-cyano-6-methylpyrimidine
[ No CAS ]
-
[ 16858-56-3 ]
Yield | Reaction Conditions | Operation in experiment |
5.2 g (24.8%) |
In ethyl acetate; acetonitrile; |
Compound 32--2-Chloro-4-cyano-6-methylpyrimidine 24.5 g of 2,4-dichloro-6-methylpyrimidine and 9.8 g of potassium cyanide were dissolved in 150 ml of CH3 CN and refluxed for 8 days. The solvent was evaporated, the residue was dissolved in 150 ml of ethyl acetate and extracted twice with 50 ml H2 O. The organic layer was dried over Na2 SO4, the solvent was evaporated and the residue was purified on silica gel using a 4:1 mixture of benzene and methyl tert.butyl ether as eluent to give 5.2 g (24.8%) of 2-chloro-4-cyano-6-methyl pyrimidine of m.p. 57 C. |
- 5
-
[ 16858-56-3 ]
-
[ 1186513-07-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
With hydroxylamine hydrochloride; triethylamine; In ethanol; at 20℃; for 1.0h; |
c) To a solution of <strong>[16858-56-3]2-chloro-6-methyl-pyrimidine-4-carbonitrile</strong> (1.25 g, 8.14 mmol) and triethylamine (3.4 mL, 24.42 mmol) in ethanol (65 mL), hydroxylamine hydrochloride (1.13 g, 16.28 mmol) is added. The reaction mixture is stirred for 1 h at rt and is then evaporated to dryness. The residue is dissolved in ethylacetate, washed with 2M aq. Na2CO3 followed by brine, dried over Na2SO4, filtered and evaporated under HV to give 2-chloro-N-hydroxy-6-methyl-pyrimidine-4-carboxamidine (1.56 g) as a yellow solid; LC-MS: tR=0.34 min; [M+1]+=187.41. |
|
With hydroxylamine hydrochloride; triethylamine; In ethanol; at 20℃; for 1.0h; |
To a solution of <strong>[16858-56-3]2-chloro-6-methyl-pyrimidine-4-carbonitrile</strong> (1.25 g, 8.14 mmol) and triethylamine (3.4 mL, 24.42 mmol) in ethanol (65 mL), hydroxylamine hydrochloride (1.13 g, 16.28 mmol) is added. The reaction mixture is stirred for 1 h at rt and is then evaporated to dryness. The residue is dissolved in ethylacetate, washed with 2M aq. Na2CO3 followed by brine, dried over Na2SO4, filtered and evaporated under HV to give 2-chloro-N-hydroxy- 6-methyl-pyrimidine-4-carboxamidine (1.56 g) as a yellow solid; LC-MS: tR = 0.34 min; [M+1]+ = 187.41. |
- 6
-
[ 64376-16-5 ]
-
[ 16858-56-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
With pyridine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20℃; for 7.0h; |
b) To a solution of 2-chloro-6-methyl-pyrimidine-4-carboxylic acid amide (1.60 g, 9.32 mmol) in DCM (160 mL), pyridine (3.0 mL, 37.30 mmol) is added. The mixture is cooled to 0 C. before trifluoroacetic anhydride (2.59 mL, 18.64 mmol) is added portionwise. Stirring is continued at 0 C. for 1 h then at rt for 6 h before the reaction is quenched with water. The mixture is diluted with DCM, and the org. phase is separated and washed with 2N aq. HCl. The aq. phase is extracted with DCM twice and the combined org. phases are washed with water followed by brine and finally are dried over MgSO4, filtered and concentrated to give 2-chloro-6-methyl-pyrimidine-4-carbonitrile (1.36 g) as a yellow solid; LC-MS: tR=0.50 min. 1H NMR (D6-DMSO): delta 2.58 (s, 3H), 8.16 (s, 1H). |
|
With pyridine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20℃; for 7.0h; |
To a solution of 2-chloro-6-methyl-pyrimidine-4-carboxylic acid amide (1.60 g, 9.32 mmol) in DCM (160 mL), pyridine (3.0 mL, 37.30 mmol) is added. The mixture is cooled to 00C before trifluoroacetic anhydride (2.59 mL, 18.64 mmol) is added portionwise. Stirring is continued at 00C for 1 h then at rt for 6 h before the reaction is quenched with water. The mixture is diluted with DCM, and the org. phase is separated and washed with 2N aq. HCI. The aq. phase is extracted with DCM twice and the combined org. phases are washed with water followed by brine and finally are dried over MgSO4, filtered and concentrated to give 2-chloro-6-methyl-pyrimidine-4-carbonitrile (1.36 g) as a yellow solid; LC-MS: tR = 0.50 min. 1H NMR (D6-DMSO): £2.58 (s, 3 H), 8.16 (s, 1 H). |
- 7
-
[ 89793-11-3 ]
-
[ 16858-56-3 ]
- 8
-
[ 89581-58-8 ]
-
[ 16858-56-3 ]
- 9
-
[ 16858-56-3 ]
-
[ 1186513-08-5 ]
- 10
-
[ 16858-56-3 ]
-
[ 1186513-21-2 ]
- 11
-
(3aR,5R,6aS)-5-(2-(trifluoromethyl)phenyl)octahydrocyclopenta[c]pyrrole hydrochloride
[ No CAS ]
-
[ 16858-56-3 ]
-
C20H19F3N4
[ No CAS ]
- 12
-
3,6-diazabicyclo [3.2.1]octan-3-yl(2-(2,2,2-trifluoroethyl)phenyl)methanone
[ No CAS ]
-
[ 16858-56-3 ]
-
6-methyl-2-(3-(2-(2,2,2-trifluoroethyl)benzoyl)-3,6-diazabicyclo[3.2.1]octan-6-yl)pyrimidine-4-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 100℃; for 16.0h;Sealed tube; |
A solution of crude 3 ,6-diazabicyclo[3 .2.1 ]octan-3-yl(2-(2,2,2-trifluoroethyl)phenyl)methanone (70 mg, 0.24 mmol, 1-2) and diisopropylethylamine (0.41 mL, 2.4 mmol) in acetonitrile (2 mL) was heated in a sealed vial at 100 C for 16 h. The reaction mixture was concentrated in vacuo and the crude residue was purified by silica gel chromatography (0-60% EtOAc in hexanes over 16 mm) to give the title compound as a foam. LRMS mlz (M+H) 416.3 found, 416.2 required. |
- 13
-
[ 185525-49-9 ]
-
[ 16858-56-3 ]
-
6-methyl-2-{1-oxo-1,3-dihydrospiro[indene-2,4'-piperidin]-1'-yl}pyrimidine-4-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
84% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 2h; Inert atmosphere; |
119.1 Step 1 : 6-methyl-2-{1 -oxo-1,3-dihydrospiro[indene-2,4'-piperidin]-1'-yl}pyrimidine-4- carbonitrile
A solution of 2-chloro-6-methylpyrimidine-4-carbonitrile(120 mg, 0.742 mmol), 1H- spiro[indene-2,4-piperidin]-3-one hydrochloride (Pharmablock, 279 mg, 1.1 14 mmol) and DIEA (303 mg, 2.23 mmol) in MeCN (5.0 ml. was stirred for 2 h at 80 under nitrogen atmosphere. The resulting mixture was concentrated under vacuum and purified by flash chromatography on silica (PE:EtOAC, 1 :1) to afford the title compound as a white solid (200 mg, 84%); LC/MS (M+1): 319.0. |