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Chemical Structure| 53106-70-0 Chemical Structure| 53106-70-0

Structure of 53106-70-0

Chemical Structure| 53106-70-0

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Product Details of [ 53106-70-0 ]

CAS No. :53106-70-0
Formula : C3H2ClNO
M.W : 103.51
SMILES Code : ClC(C=O)C#N
MDL No. :MFCD20621600
InChI Key :RJOJHKXZYVLLKN-UHFFFAOYSA-N
Pubchem ID :11137111

Safety of [ 53106-70-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H301+H311+H331-H315-H319-H335
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338-P311
Class:6.1(3)
UN#:3275
Packing Group:

Application In Synthesis of [ 53106-70-0 ]

* 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.

  • Downstream synthetic route of [ 53106-70-0 ]

[ 53106-70-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 100643-27-4 ]
  • [ 53106-70-0 ]
  • [ 69205-79-4 ]
YieldReaction ConditionsOperation in experiment
10.11 g With sodium acetate; In water; at 100℃;Inert atmosphere; Methyl formate (18.0 mL, 17.48 g, 291.4 mmol) in toluene (8 mL) was added at 0 C to a stirred suspension ofNaOMe (14.30 g, 264.9 mmol) in toluene (200 mL). This was followed by dropwise addition of chloroacetonitrile (16.8 mL, 20.00 g, 264.9 mmol) in toluene (60 mL) over 1 h. The reaction mixture was stirred for 3 h followed by addition of H2O (150 mL). The organic layer was separated and the aqueous layer was acidified to pH 5 using 6 M HCl and subsequently extracted with EtOAc (3 × 100 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo (40 C, 70 mbar). The dark residue was suspended in H2O (60 mL) and added to a solution of NaOAc (16.39 g, 199.8 mmol) and 2,6-diaminopyrimidin-4(3H)-one(12.00 g, 95.2 mmol) in H2O (200 mL) (previously stirred at 100 C until complete dissolution). The reaction was refluxed for 16 h. After cooling to room temperature the suspension was filtered and washed with H2O (2 ×20 mL), acetone (2 × 10 mL) and Et2O (2 × 40 mL) to yield 1 (10.11 g, 60%) as a light tan solid.
  • 2
  • [ 100643-27-4 ]
  • [ 53106-70-0 ]
  • [ 69205-79-4 ]
  • 2-Amino-6-hydroxy-4-oxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile [ No CAS ]
  • 3
  • [ 53106-70-0 ]
  • [ 56-06-4 ]
  • [ 69205-79-4 ]
YieldReaction ConditionsOperation in experiment
40% Preparation 4: 2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine- 5-carbonitrile 2,4-Diamino-6-hydroxypyrimidine (3.00 g, 24 mmol) was added to a solution of sodium acetate (6.4g, 76 mmol) in millipore water (90 mL) and stirred at 50 C for 1 hour. While still at 50 C a solution of crude chloro(formyl)acetonitrile (3.00 g,32 mmol) in mQ water (44 mL) was added dropwise with a dropping funnel, during which time the reaction turned beigeand heating continued for 18 h at 50 C, after which time the reaction was heated to 100 C for 3 h. The reaction mixture was allowed to cool to room temperature and the solid removed by filtration. The solid was suspended in EtOH and SM aqueous KOH solution was added until the soliddissolved. Charcoal was added to the solution and the mixture stirred for 30 minutes before removal of the solid by filtration. The pH of the filtrate was adjusted to pH=6 with concentrated aqueous HCI solution during which time a precipitate formed and was collected by filtration. In order to remove the final traces of water from the solid it was dissolved in a mixture of toluene/methanol 1/1 and thenconcentrated at reduced pressure. The resultant solid was dried over P205 to afford the desired compound (1.68 g, 9.6 mmol, 40% yield) as beige solid. Procedure based on Brooks 2012.OH (400 MHz, DMSO-d6) 0 11.98 (br s, 1H) 10.74 (br s, 1H), 7.59 (s, 1H), 6.43 (s, 2H).Oc(100 MHz, DMSO-d6) 0 158.0, 154.3, 152.1, 128.2, 116.4, 99.2, 86.0. HRMS (m/z ESI): C7H5N50 EM-H]- Found 174.0415 Requires: 174.0416.
1.68 g With sodium acetate; In water; at 50 - 100℃; for 22h; 2,4-Diamino-6-hydroxypyrimidine (3.00 g, 24 mmol) was added to a solution of sodium acetate (6.4g, 76 mmol) in millipore water (90 ml.) and stirred at 50 C for 1 hour. While still at 50 C a solution of crude chloro(formyl)acetonitrile (3.00 g, 32 mmol) in mQ water (44 ml.) was added dropwise with a dropping funnel, during which time the reaction turned beige and heating continued for 18 h at 50 C, after which time the reaction was heated to 100 C for 3 h. The reaction mixture was allowed to cool to room temperature and the solid removed by filtration. The solid was suspended in EtOH and 5M aqueous KOH solution was added until the solid dissolved. Charcoal was added to the solution and the mixture stirred for 30 minutes before removal of the solid by filtration. The pH of the filtrate was adjusted to pH=6 with concentrated aqueous HCI solution during which time a precipitate formed and was collected by filtration. In order to remove the final traces of water from the solid it was dissolved in a mixture of toluene/methanol 1/1 and then concentrated at reduced pressure. The resultant solid was dried over P2O5 to afford the desired compound (1.68 g, 9.6 mmol, 40% yield) as beige solid. Procedure based on Brooks 2012. deltaEta (400 MHz, DMSO-tfe) delta 11.98 (br s, 1H) 10.74 (br s, 1H), 7.59 (s, 1H), 6.43 (s, 2H). deltaalpha (100 MHz, DMSO-tfe) delta 158.0, 154.3, 152.1, 128.2, 116.4, 99.2, 86.0. HRMS (m/z ESI ) : C7H5N5O [M-H]" Found 174.0415 Requires: 174.0416.
 

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Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Blaise Reaction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Heat of Combustion • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Thorpe-Ziegler Reaction • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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