Water → 2-[[7-[[Dimethyl(oxo)-lambda6-sulfanylidene]amino]-5-methyl-quinazolin-4-yl]amino]-5-fluoro-phenol

HRID 1396651Notes

Reaction equation

HRID 1396651 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([N:28]=[S:29]([CH3:32])([CH3:31])=[O:30])=[CH:24][C:25]=2[CH3:27])[N:20]=[CH:19][N:18]=1)C1C=CC=CC=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH3:32][S:29](=[N:28][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([NH:16][C:10]3[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=3[OH:8])=[N:18][CH:19]=[N:20]2)=[C:25]([CH3:27])[CH:24]=1)([CH3:31])=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86718469N-(2-benzyloxy-4-fluoro-phenyl)-7-[[dimethyl(oxo)-lambda6-sulfanylidene]amino]-5-methyl-quinazolin-4-amine

Product 1

HCID 867184712-[[7-[[Dimethyl(oxo)-lambda6-sulfanylidene]amino]-5-methyl-quinazolin-4-yl]amino]-5-fluoro-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.5 g (7.8 mmol) of N-(2-benzyloxy-4-fluoro-phenyl)-7-[[dimethyl(oxo)-λ6-sulfanylidene]amino]-5-methyl-quinazolin-4-amine in DCM are cooled to 0° C., 0.9 ml (9.3 mmol) boron tribromide are added dropwise and the reaction mixture is stirred for 15 min. Water is added cautiously and the aqueous layer is separated and extracted with DCM. The organic phases are pooled, washed with water, dried and evaporated. The residue is treated with isopropanol, filtered and dried.

Workup

  1. customthe aqueous layer is separated
  2. extractionextracted with DCM
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. additionThe residue is treated with isopropanol
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-fb0d626ec6fd43b18ed4ac4e8b1c6013
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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