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6-(Bromomethyl)-4-chloroquinazoline → HCID 86757280, compound

HRID 651632
Notes
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Reaction equation

HRID 651632 reaction equation
[CH3:1][N:2]([C@H:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23])[S:3]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[CH:7]=1)(=[O:5])=[O:4].[Li]N([Si](C)(C)C)[Si](C)(C)C.Br[CH2:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[CH:41][N:40]=[C:39]2[Cl:46]>C1COCC1>[Cl:46][C:39]1[C:38]2[C:43](=[CH:44][CH:45]=[C:36]([CH2:35][N:20]3[CH2:21][CH2:22][C@H:18]([N:2]([CH3:1])[S:3]([C:6]4[CH:15]=[CH:14][C:13]5[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=5)[CH:7]=4)(=[O:5])=[O:4])[C:19]3=[O:23])[CH:37]=2)[N:42]=[CH:41][N:40]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 219419376-(Bromomethyl)-4-chloroquinazolineHCID 54147218HCID 54147218, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 86757280HCID 86757280, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-methoxynaphthalene-2-sulfonic acid methyl-(2-oxopyrrolidin-3-(S)-yl)-amide (0.35 g, 1.04 mmol) in THF (7 mL) at 0° C. is added LiN(SiMe3)2 (1 mL, 1 mmol, 1 M solution in THF). The solution is stirred at 0° C. for 40 minutes. After this time, 6-bromomethyl-4-chloro-quinazoline (0.24 g, 0.94 mmol) is added. The resulting solution is stirred for 4 hours. The reaction is quenched by the addition of a saturated NH4Cl solution. The solution is diluted with EtOAc and water. The layers are separated. The organic layer is washed with water and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 20% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2 to give the title compound (0.25 g, 0.49 mmol) as a white solid.

Workup

  1. stirringThe resulting solution is stirred for 4 hours
  2. customThe reaction is quenched by the addition of a saturated NH4Cl solution
  3. additionThe solution is diluted with EtOAc and water
  4. customThe layers are separated
  5. washThe organic layer is washed with water and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by column chromatography
  10. washeluting with a gradient of 20% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-3acea98b22f4471a92a260e8f994e6c5
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06281227B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes