4-DIMETHOXYMETHYLPYRIMIDIN-2-YLAMINE

Pyruvic aldehyde dimethyl acetal (10 g, 84 mmol) and N, N’-dimethyl formamide dimethyl diacetal (10 g, 84 mmol) in DMF (30 ml) were heated in a round bottom flask at 110 °C for 15 h. Guanidine hydrochloride (12 g, 127 mmol) and NaOH (6.7 g, 169 mmol) in water were then added to the reaction mixture. The mixture was refluxed for further 36 h. The reaction mass was then cooled and filtered. The product was recrystallized from hot ethyl acetate to yield white crystalline solid 2 (10 g, 70percent).Procedure H: Intermediate 8 (1-8) - 2-Aminopyrimidine-4-carboxaldehyde dimethylacetal.; [0093] A solution of 5.5 mL (41 mmol, 1.0 eq.) of dimethylformamide dimethyl acetal and 5.0 mL (41 mmol, 1.0 eq.) pyruvric aldehyde dimethyl acetal was heated at 100 a) a Compounds A solution of 2.5 g (15 mmol, 1.0 eq.) Procedure I: Intermediate 9 (1-9) - 2-Aminopyrimidine-4-carboxaldehyde.; [0095] A solution of 2.5 g (15 mmol, 1.0 eq.) of 2-aminopyrimidine-4- carboxaldehyde dimethylacetal (1-8) in 16 mL (48 mmol, 3.2 eq.) of 3M HCl was heated at 48 0C for 14 h. The mixture was allowed to cool to room temperature and diluted with 50 mL of EtOAc. The aqueous layer was neutralized with NaHCCb and then extracted with EtOAc (5 x 50 mL). The combined organic extracts were dried (Na2SO^ and the solvent removed in vacuo to provide 0.69 g (5.6 mmol, 37percent) of 2- aminopyrimidine-4-carboxaldehyde (1-9) as a yellow solid.2-Aminopyrimidine-4-carboxaldehyde dimethylacetal.; A solution of 5.5 ml (41 mmol, 1 eq.) of dimethylformamide dimethyl acetal and 5.0 ml (41 mmol, 1 eq.) pyrvuric aldehyde dimethyl acetal was heated at 100 C. for 16 h. Methanol was removed in vacuo to afford an oil. A solution of NaOH (1.8 g, 45 mmol, 1.1 eq.) in 5 mL of H2O was added to a solution of 4.3 g (45 mmol, 1.1 eq.) of guanidine HCl in 10 mL of H2O. The resulting solution was added to the above described oil. The resulting mixture was stirred at r.t. for 48 h. Filtration afforded 2.5 g (50%) of To the stirred mixture of 2.29 g of guanidine hydrochloride (24.0 mmol) and 8 mL of methanol 1.30 g sodium methoxide (24.0 mmol) and 3.46 g Preparation 9a1 (20.0 nnnol) were added, then stirred at 75 C for 2 h. The reaction mixture was cooled, concentrated under reduced pressure, then 30 mL water was added. The formed precipitate was filtered, washed with water and dried to give 2-Aminopyrimidine-4-carboxaldehyde dimethylacetal.; A solution of 5.5 ml (41 mmol, 1 eq.) of dimethylformamide dimethyl acetal and 5.0 ml (41 mmol, 1 eq.) pyrvuric aldehyde dimethyl acetal was heated at 100° C. for 16 h. Methanol was removed in vacuo to afford an oil. A solution of NaOH (1.8 g, 45 mmol, 1.1 eq.) in 5 mL of H2O was added to a solution of 4.3 g (45 mmol, 1.1 eq.) of guanidine HCl in 10 mL of H2O. The resulting solution was added to the above described oil. The resulting mixture was stirred at r.t. for 48 h. Filtration afforded 2.5 g (50percent) of To the stirred mixture of 2.29 g of guanidine hydrochloride (24.0 mmol) and 8 mL of methanol 1.30 g sodium methoxide (24.0 mmol) and 3.46 g Preparation 9a1 (20.0 nnnol) were added, then stirred at 75 °C for 2 h. The reaction mixture was cooled, concentrated under reduced pressure, then 30 mL water was added. The formed precipitate was filtered, washed with water and dried to give General procedure: Reactions were performed with 0.30 mmol of

Molecular Weight:169.18
XLogP3:-0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:169.085126602
Monoisotopic Mass:169.085126602
Topological Polar Surface Area:70.3
Heavy Atom Count:12
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes