Bromomethylcyclopropane → 2-Chloro-5-(cyclopropylmethyl)-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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Reaction Steps

To a round-bottom flask was added 2-chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x20, 248 mg, 1.030 mmol) in DMSO (4 mL). Sodium tert-butoxide (119 mg, 1.236 mmol) was added, followed by (bromomethyl)cyclopropane (0.105 mL, 1.082 mmol), and the reaction mixture was stirred overnight at room temperature. The mixture was subsequently filtered and the filtrate was purified by preparatory HPLC using a gradient of 25-50% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The fractions were collected and concentrated in vacuo to give the title compound as a brown solid (56 mg, 0.190 mmol, 18%). ESI-MS m/z [M+H]+ calc'd for C14H19ClN4O, 295.12; found 295.6.

Provenance & Evidence