Methanol → N4-(3-ethynylphenyl)quinazoline-4,7-diamine

HRID 1288864노트

반응식

HRID 1288864 반응식
Cl.[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([N+:21]([O-])=O)=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)#[CH:3].CO.C(Cl)(Cl)Cl.P([O-])(O)O.[Na+]>O1CCCC1.[Pd].O>[NH2:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:2]#[CH:3])[CH:5]=3)=[N:12][CH:13]=[N:14]2)=[CH:19][CH:18]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 6212ChloroformHCID 18925068HCID 18925068, 화합물HCID 23701735Sodium dihydrogen phosphite

생성물 1

HCID 16045588N4-(3-ethynylphenyl)quinazoline-4,7-diamine

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

The title product of example 12 (1.039 g, 3.18 mmol) was dissolved in 50 mL of tetrahydrofuran, 10 mL of methanol and 5 mL of chloroform at 50° C. Sodium dihydrogen phosphite (NaH2PO2, 3.822 g, 36 mmol) and 10% palladium on carbon (0.19 g) were added followed by dropwise addition of 10 mL of water. When 3 mL of water had been added the mixture became noticeably more homogeneous. After 1 hour the mixture was filtered through Celite. The Celite was washed thoroughly with methanol and chloroform. The combined organic solutions were vacuum evaporated to a residue which was triturated with water, 3% aqueous sodium bicarbonate and filtered. The solid title product was washed with water then diethyl ether and dried in vacuo, 1.054 gm (127%, wet). A portion of the above product was recrystallized from a minimum amount of hot ethanol and water to give, after removal of a small first crop of impure material, pure title product, (43%), mp 180° C. (dec).

후처리

  1. customat 50° C
  2. filtrationAfter 1 hour the mixture was filtered through Celite
  3. washThe Celite was washed thoroughly with methanol and chloroform
  4. customevaporated to a residue which
  5. customwas triturated with water, 3% aqueous sodium bicarbonate
  6. filtrationfiltered
  7. washThe solid title product was washed with water
  8. dry with materialdiethyl ether and dried in vacuo, 1.054 gm (127%, wet)
  9. customA portion of the above product was recrystallized from a minimum amount of hot ethanol and water
  10. customto give
  11. customafter removal of a small first crop of impure material, pure title product, (43%), mp 180° C. (dec)

출처 및 근거

ORD 기록
ord-294dfa3f47e449658e41cb906b97a7b7
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05747498

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