Water → HCID 11255766, compound

HRID 1765029Notes

Reaction equation

HRID 1765029 reaction equation
[CH3:1][N:2]1[C:14]2[C:13]([C:15]3[S:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[CH:12][C:11]3[C:6](=[C:7]([NH2:22])[N:8]=[C:9]([NH2:21])[N:10]=3)[C:5]=2[CH:4]=[CH:3]1.[H-].[Na+].I[CH3:26].O>CN(C)C=O>[CH3:1][N:2]1[C:14]2[C:13]([C:15]3[S:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[CH:12][C:11]3[C:6](=[C:7]([NH:22][CH3:26])[N:8]=[C:9]([NH2:21])[N:10]=3)[C:5]=2[CH:4]=[CH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11426862HCID 11426862, compound

Product 1

HCID 11255766HCID 11255766, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 7-methyl-6-(5-methyl-thiophen-2-yl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (100 mg, 0.32 mmol) in N,N-dimethylformamide (5.0 mL) at 25° C. was treated with 60% sodium hydride (25 mg, 0.62 mmol) and iodomethane (0.62 mL, 0.35 mmol) and stirred at 25° C. for 15 min. The resulting mixture was poured into water and extracted with a 9/1 methylene chloride/methanol solution. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 9:1 methylene chloride/methanol) afforded 7,N1-dimethyl-6-(5-methyl-thiophen-2-yl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (12 mg, 11.5%) as a light yellow solid; EI-HRMS m/e calcd for C17H17N5S (M+H)+ 324.1278, found 324.1280; and 7,N1,N1-trimethyl-6-(5-methyl-thiophen-2-yl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (18 mg, 16.5%) as a dark brown solid; EI-HRMS m/e calcd for C18H19N5S (M+H)+ 338.1434, found 338.1437.

Workup

  1. extractionextracted with a 9/1 methylene chloride/methanol solution

Sources & evidence

ORD record
ord-695ed2ae75e2470187409ed2eb5eccd3
Source dataset
uspto-grants-2007_06
Patent number
US07226915B2

Reaction notes

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