Methyl iodide → HCID 21106341, compound

HRID 1765026Notes

Reaction equation

[I:1][C:2]1[C:3]2[NH:16][CH:15]=[CH:14][C:4]=2[C:5]2[C:10]([CH:11]=1)=[N:9][C:8]([NH2:12])=[N:7][C:6]=2[NH2:13].[OH-].[Na+].I[CH3:20]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:1][C:2]1[C:3]2[N:16]([CH3:20])[CH:15]=[CH:14][C:4]=2[C:5]2[C:10]([CH:11]=1)=[N:9][C:8]([NH2:12])=[N:7][C:6]=2[NH2:13]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution 6-iodo-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine VI (2.68 g, 8.24 mmol) in tetrahydrofuran (100 mL) was treated with powdered sodium hydroxide (0.66 g, 16.5 mmol), iodomethane (0.62 mL, 9.96 mmol), and tetrabutylammonium bromide (0.8 g, 2.48 mmol) and the resulting mixture stirred at 25° C. for 18 h. The resulting mixture was concentrated in vacuo. The residue was partitioned between methylene chloride (70 mL) and water (70 mL) and this mixture was stirred at 25° C. for 30 min. The precipitate was isolated by filtration, washed with water, and dried in vacuo to afford 6-iodo-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (2.67 g, 95.5%) as a yellow solid; 1H NMR (DMSO-d6, 300 MHz) δ 7.58 (s, 1H), 7.47 (d, J=2.93 Hz, 1H), 6.99 (d, J=2.93 Hz, 1H), 6.78 (broad s, 2H), 5.83 (broad s, 2H), 4.16 (s, 3H).

Workup

concentrationThe resulting mixture was concentrated in vacuo
customThe residue was partitioned between methylene chloride (70 mL) and water (70 mL)
stirringthis mixture was stirred at 25° C. for 30 min
customThe precipitate was isolated by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-885b23a85f794d33a32a3157d66dcdd3
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226915B2

Reaction notes

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