2-Bromopropane → 7-Isopropoxy-6-methoxy-4-(3'-methylanilino)quinazoline

HRID 2210019Notes

Reaction equation

HRID 2210019 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:24][CH3:25])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 136066186HCID 136066186, compound

Product 1

HCID 199631757-Isopropoxy-6-methoxy-4-(3'-methylanilino)quinazolineYield 86.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Isopropyl bromide (0.246 g) was added to a stirred mixture of 7-hydroxy-6-methoxy-4-(3'-methylanilino)quinazoline (0.281 g), potassium carbonate (0.414 g) and DMA (3 ml). The mixture was stirred at ambient temperature for 30 minutes and then heated to 70° C. for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 7-isopropoxy-6-methoxy-4-(3'-methylanilino)quinazoline (0.28 g), m.p. 218°-221° C. NMR Spectrum: (CD3SOCD3) 1.36 (d, 6H), 2.34 (s, 3H), 3.94 (s, 3H), 4.83 (m, 1H), 6.94 (d, 1H), 7.17 (s, 1H), 7.27 (t, 1H), 7.57 (s, 1H), 7.64 (d, 1H), 7.82 (s, 1H), 8.43 (s, 1H); Elemental Analysis: Found C, 69.4; H, 6.7; N, 12.0; C19H21N3O2. 0.3H2O. 0.1EtOAc requires C, 69.0; H, 6.6; N, 12.4%.

Workup

  1. temperatureheated to 70° C. for 1 hour
  2. customThe mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-501f06f403e14e6f9c560b4f7b3c468b
Source dataset
uspto-grants-1995_10
Patent number
US05457105

Reaction notes

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