Carbonic acid-guanidine (1:1) → 1-{1-[4-(2,4-diamino-6-phenylpyrido[2,3-d]pyrimidin-7-yl)benzyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one

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Reaction Conditions

Reaction Steps

Guanidine carbonate (0.036 g, 0.2 mmol) was added to a suspension of potassium tert-butoxide (0.045 g, 0.4 mmol) in dimethylacetamide (1.0 mL). The mixture was stirred at 50° C. for 10 min. Then 2-chloro-6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (11-5) (0.052 g, 0.1 mmol) was added. The mixture was then heated to 140° C. for 20 min in microwave. Purification directly with reverse phase HPLC (5–100% CH3CN/H2O+0.1% TFA) gave 1-{1-[4-(2,4-diamino-6-phenylpyrido[2,3-d]pyrimidin-7-yl)benzyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (11-6) as a off-white solid. 1H NMR (DMSO-d6) δ 8.59 (s, 1H), 8.45 (broad, 4H), 6.91–7.34 (m, 13H), 4.17–4.21(m, 1H), 3.60 (m, 4H), 3.34 (m, 2H), 2.38 (m, 2H), 2.12–2.23 (m, 2H). LRMS m/z (M+H) Calcd: 543.6, found: 543.2.

Provenance & Evidence