Water → HCID 21260357, compound

HRID 634680Notes

Reaction equation

HRID 634680 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][C:16]1[C:17]([CH3:40])=[CH:18][C:19]([F:39])=[C:20]([CH:38]=1)[NH:21][C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34]CCO)=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:5]([O:4][CH2:1][CH2:2][O:34][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([NH:21][C:20]3[CH:38]=[C:16]([O:15][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:17]([CH3:40])=[CH:18][C:19]=3[F:39])=[N:23][CH:24]=[N:25]2)=[CH:30][C:29]=1[O:32][CH3:33])(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21260315HCID 21260315, compound

Product 1

HCID 21260357HCID 21260357, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (55 ml, 0.58 mmol) was added to a mixture of 4-(5-benzyloxy-2-fluoro-4-methylanilino)-7-(2-hydroxyethoxy)-6-methoxyquinazoline (233 mg, 0.52 mmol), triethylamine (80 ml, 0.57 mmol) and 4-(N,N-dimethylamino)pyridine (5 mg) in ethyl acetate (50 ml). The mixture was stirred for 2 hours at ambient temperature, water was added, the organic layer separated, washed with water and brine and dried (MgSO4). Most of the solvent was removed by evaporation and hexane added. The precipitated product was collected by filtration to give 7-(2-acetoxyethoxy)-4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline (110 mg, 43%).

Workup

  1. customthe organic layer separated
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. customMost of the solvent was removed by evaporation and hexane
  5. additionadded
  6. filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-49faa64bc1db4eb68ea9706cf597c785
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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