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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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