Triethylamine → 4-(1,3-Dihydroisoindol-2-yl)-6-iodoquinazoline

HRID 1469088Notes

Reaction equation

HRID 1469088 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:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][NH:14]1.C(N(CC)CC)C.N1C2C(=CC=CC=2)C=NC=1>O1CCOCC1>[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[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 8471TriethylamineHCID 9210QuinazolineHCID 422478IsoindolineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 675144384-(1,3-Dihydroisoindol-2-yl)-6-iodoquinazolineYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.50 g of 4-chloro-6-iodoquinazoline, 0.27 g of 2,3-dihydro-1H-isoindole, 0.42 ml of triethylamine in 4 ml of dioxane are heated at 80° C. in a flask until the quinazoline has reacted virtually completely (HPLC check, about 3 hours). The cooled reaction solution is evaporated to dryness in a rotary evaporator. The residue is suspended in EA. The undissolved solid is filtered off, rinsed with water and dried, giving 0.56 g of 4-(1,3-dihydroisoindol-2-yl)-6-iodoquinazoline as slightly yellowish solid (yield 93%, content 94%); MS-FAB (M+H+)=373.8; Rf (polar method): 1.73 min. This is employed for the next step without further purification.

Workup

  1. customhas reacted virtually completely (HPLC check, about 3 hours)
  2. customThe cooled reaction solution
  3. customis evaporated to dryness in a rotary evaporator
  4. filtrationThe undissolved solid is filtered off
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-9bb20bbb8a2f413f8d12185ffbcda66a
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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