Morpholine → HCID 19963176, compound

HRID 2210018Notes

Reaction equation

HRID 2210018 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:23][CH3:24].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH3:24][O:23][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[O:4][CH2:3][CH2:2][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[N:12]=[CH:11][N:10]=[C:9]2[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 19963119HCID 19963119, compound

Product 1

HCID 19963176HCID 19963176, compound

Procedure

A mixture of 7-(2-bromoethoxy)-6-methoxy-4-(3'-methylanilino)quinazoline (0.25 g) and morpholine (4 ml) was stirred at ambient temperature for 4 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a dilute aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4) and evaporated. The residue was triturated under diethyl ether to give 6-methoxy-4-(3'-methylanilino)-7-(2-morpholinoethoxy)quinazoline (0.198 g), m.p. 168°-170° C. NMR Spectrum: (CD3SOCD3 +CD3CO2D) 2.35 (s, 3H), 3.15 (t, 4H), 3.81 (t, 4H), 3.96 (s, 3H), 6.93 (d, 1H), 7.21 (s, 1H), 7.26 (t, 1H), 7.58 (s, 1H), 7.63 (d, 1H), 7.84 (s, 1H), 8.44 (s, 1H), 9.58 (s, 1H); Elemental Analysis: Found C, 64.3; H, 6.9; N, 13.8; C22H26N4O3. 0.9H2O requires C, 64.3; H, 6.8; N, 13.6%.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated under diethyl ether

Sources & evidence

ORD record
ord-5c99a0aba0424fe98ec86faf033c942d
Source dataset
uspto-grants-1995_10
Patent number
US05457105

Reaction notes

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