Triethylamine → 6-iodo-4-(7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)quinazoline

HRID 1469107Notes

Reaction equation

HRID 1469107 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.[CH3:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][NH:21][CH2:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C.N1C2C(=CC=CC=2)C=NC=1>O1CCOCC1.CC(=O)OCC>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[N:21]1[CH2:20][CH2:19][C:18]2[C:23](=[CH:24][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH2:22]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9210QuinazolineHCID 4172887-Methoxy-1,2,3,4-TetrahydroisoquinolineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 680263256-iodo-4-(7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)quinazolineYield 57%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

0.75 g of 4-chloro-6-iodoquinazoline, 0.58 g of 7-methoxy-1,2,3,4-tetrahydroisoquinoline and 0.64 ml of triethylamine in 5 ml of dioxane are heated at 80° C. in a flask until the quinazoline has reacted completely (HPLC check, about 2 hours). The cooled reaction solution is diluted with EA and washed 3 times with water. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 5-100% in 22 min.), giving 0.60 g of 6-iodo-4-(7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)quinazoline as yellowish solid (yield 57%, content 93%); MS-FAB (M+H+)=418.0; Rf (polar method): 1.87 min.

Workup

  1. customhas reacted completely (HPLC check, about 2 hours)
  2. customThe cooled reaction solution
  3. washwashed 3 times with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. custompurified by means of column chromatography (gradient heptane: EA 5-100% in 22 min.)

Sources & evidence

ORD record
ord-bd847ea177e24a73bb81388f8fbc9440
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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