Quinazoline → HCID 67514332, compound

HRID 1469103Notes

Reaction equation

HRID 1469103 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1.N1C2C(=CC=CC=2)C=NC=1>O1CCOCC1.CC(=O)OCC>[N:13]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 9210QuinazolineHCID 694601,2,3,4-TetrahydroquinolineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 67514332HCID 67514332, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.30 g of 4-chloro-6-iodoquinazoline, 1.50 ml of 1,2,3,4-tetrahydroquinoline in 10 ml of dioxane are heated at 110° C. in a flask until the quinazoline has reacted completely (HPLC check, about 3 hours). The cooled reaction solution is diluted with EA and washed 3 times with 5% citric acid. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 0-100% in 18 min.), giving 1.27 g of 4-(3,4-dihydro-2H-quinolin-1-yl)-6-iodoquinazoline as yellowish solid (yield 81%, content 99%); MS-FAB (M+H+)=388.0; Rf (polar method): 2.89 min.

Workup

  1. customhas reacted completely (HPLC check, about 3 hours)
  2. customThe cooled reaction solution
  3. washwashed 3 times with 5% citric acid
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. custompurified by means of column chromatography (gradient heptane: EA 0-100% in 18 min.)

Sources & evidence

ORD record
ord-07fed750c5cd4b0d9c8371a83f2603b9
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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