1-Butanol → HCID 11294944, compound

HRID 411290Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6](C)=[C:7](C)[CH:8]=2)[N:3]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25]([CH2:34][NH:35][CH3:36])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:37](=[O:40])([O-])[O-].[K+].[K+].[CH2:43]([OH:47])CCC>>[CH2:15]([N:22]1[CH2:23][CH2:24][C:25]([CH2:34][N:35]([CH3:36])[C:2]2[N:11]=[C:10]([NH2:12])[C:9]3[C:4](=[CH:5][C:6]([O:40][CH3:37])=[C:7]([O:47][CH3:43])[CH:8]=3)[N:3]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:27]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Reactant 4

HCID 2631-Butanol

HCID 11430Potassium Carbonate

HCID 11426409HCID 11426409, compound

HCID 185407744-Amino-2-chloro-6,7-dimethylquinazoline

Product 1

HCID 11294944HCID 11294944, compound

Procedure

A mixture of 2-chloro-6,7-dimethyl-quinazolin-4-ylamine 1 (X=Cl) (900 mg), (1-benzyl-4-phenyl-piperidin-4-ylmethyl)-methyl-amine 2a (R1=CH3 and R2=phenyl) (440 mg) and potassium carbonate (250 mg) in 1-butanol (20 ml) was refluxed for 18 hours. The cooled reaction mixture was filtered, the filtrate was evaporated, and the residue was distributed between water and dichloromethane. The organic phase was dried over potassium carbonate, filtered, and evaporated. The residue was purified by flash chromatography on silica gel to provide 1.3 g of N2-(1-Benzyl-4-phenyl-piperidin-4-ylmethyl)-6,7-dimethoxy-N2-methyl-quinazoline-2,4-diamine 10, as an oil, MS: 485 (M+).

Workup

customThe cooled reaction mixture
filtrationwas filtered
customthe filtrate was evaporated
dry with materialThe organic phase was dried over potassium carbonate
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-bf6a08d9250a42e684b2ac02f805af77
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559153B2

Reaction notes

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