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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 69205-79-4 |
| Formula : | C7H5N5O |
| M.W : | 175.15 |
| SMILES Code : | N#CC1=CNC(N=C(N)N2)=C1C2=O |
| MDL No. : | MFCD13178502 |
| InChI Key : | FMKSMYDYKXQYRV-UHFFFAOYSA-N |
| Pubchem ID : | 135446206 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H332-H335 |
| Precautionary Statements: | P280-P305+P351+P338-P310 |
* 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 |
|---|---|---|
| 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. |
[ 6974-32-9 ]
[ 69205-79-4 ]
[ 108-24-7 ]
[ 69205-79-4 ]
[ 69205-79-4 ]
[ 106-95-6 ]
[ 69205-79-4 ]
[ 106-54-7 ]
| Yield | Reaction Conditions | Operation 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. |
[ 69205-79-4 ]
[ 69205-79-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 53% | With pyridine; at 90℃; for 48h;Inert atmosphere; | In a dry round bottomed flask under an atmosphere of argon, trityl chloride (1.20 g, 4.28 mmol) was added to a solution of <strong>[69205-79-4]2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile</strong> (0.50 g, 2.85 mmol) in dry pyridine (29 mL). The mixture reaction was heated at 90 C for 48 h. The reaction mixture was concentrated under reduced pressure then absorbed on silica gel and purified by flash chromatography on silica gel eluting with dichloromethane/MeOH with a gradient starting at 2% of MeOH and rising to lO%. The desired compound wasobtained as a brown solid (0.63 g, 1.5 mmol, 53% yield).Procedure based on Olgen 2008.OH (400 MHz, DMSO-d6) oe 11.80 (br s, 1H); 10.64 (br s, 1H), 7.56 (s, 1H), 7.41(s, 1H), 7.29-7.28 (m, 12H), 7.23-7.17 (m, 3H), 5.73 (s, 1H).HRMS (m/z ESI): C26H18N50 [M-H] Found 416.1514 Requires: 416.1511. |
| 53% | With pyridine; at 90℃; for 48h;Inert atmosphere; | In a dry round bottomed flask under an atmosphere of argon, trityl chloride (1.20 g, 4.28 mmol) was added to a solution of 2-amino-4,7-dihydro-4-oxo-3A/- pyrrolo[2,3-d]pyrimidine-5-carbonitrile (0.50 g, 2.85 mmol) in dry pyridine (29 ml_). The mixture reaction was heated at 90 C for 48 h. The reaction mixture was concentrated under reduced pressure then absorbed on silica gel and purified by flash chromatography on silica gel eluting with dichloromethane/MeOH with a gradient starting at 2% of MeOH and rising to 10%. The desired compound was obtained as a brown solid (0.63 g, 1.5 mmol, 53% yield). Procedure based on Olgen 2008. deltaEta (400 MHz, DMSO-de) delta 11.80 (br s, 1H); 10.64 (br s, 1H), 7.56 (s, 1H), 7.41(s, 1H), 7.29-7.28 (m, 12H), 7.23-7.17 (m, 3H), 5.73 (s, 1H). HRMS (m/z ESI+) : C26Hi8N50 [M-H]+ Found 416.1514 Requires: 416.1511. |