1,2,3,4-Tetrahydroisoquinoline → HCID 67516832, compound

HRID 1469100Notes

Reaction equation

HRID 1469100 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.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1.C(N(CC)CC)C.N1C2C(=CC=CC=2)C=NC=1>O1CCOCC1>[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]1[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

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 9210QuinazolineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 67516832HCID 67516832, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.75 g of 4-chloro-6-iodoquinazoline, 0.45 g of 1,2,3,4-tetrahydroisoquinoline and 0.63 ml of triethylamine in 6.0 ml of dioxane are heated at 80° C. in a flask until the quinazoline has reacted completely (HPLC check, about 3 hours). The cooled reaction solution is evaporated to dryness in a rotary evaporator. The residue is purified by means of column chromatography (gradient heptane: EA 10-100% in 20 min.), giving 0.87 g of 4-(3,4-dihydro-1H-isoquinolin-2-yl)-6-iodoquinazoline as yellowish solid (yield 90%, content 92%); MS-FAB (M+H+)=388.0; Rf (polar method): 1.84 min.

Workup

  1. customhas reacted completely (HPLC check, about 3 hours)
  2. customThe cooled reaction solution
  3. customis evaporated to dryness in a rotary evaporator
  4. customThe residue is purified by means of column chromatography (gradient heptane: EA 10-100% in 20 min.)

Sources & evidence

ORD record
ord-9c1d5e2264a14700963927a06fcbca21
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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