Potassium Carbonate → HCID 178501760, compound

HRID 1672484Notes

Reaction equation

HRID 1672484 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[C:12]([OH:20])[C:13]([CH3:19])=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH3:27][O:28][C:29](=[O:32])[CH2:30]Br>CN(C=O)C.O>[OH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[C:12]([O:20][CH2:30][C:29]([O:28][CH3:27])=[O:32])[C:13]([CH3:19])=[CH:14][CH:15]=3)[N:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178422922HCID 178422922, compound

Product 1

HCID 178501760HCID 178501760, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-[(trans-4-hydroxycyclohexyl)amino]-7-methylquinazolin-8-ol (20 g, 0.073 mol) in DMF (160 mL) was added K2CO3 (10.6 g, 0.077 mol) in one portion at room temperature. Then a solution of bromoacetic acid methyl ester (11.5 g, 0.075 mol) in DMF (40 mL) was added dropwise. After the addition, the reaction mixture was stirred at room temperature overnight. The mixture was diluted with water (400 mL) and extracted with EtOAc (200 mL×3). The combined organic layers were washed with water (150 mL), dried over anhydrous Na2SO4 and evaporated in vacuo to give the crude product. The crude product was re-crystallized from EtOH (150 mL) to give the title compound (13 g, 51.4%) as an off-white solid.

Workup

  1. additionAfter the addition
  2. extractionextracted with EtOAc (200 mL×3)
  3. washThe combined organic layers were washed with water (150 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customThe crude product was re-crystallized from EtOH (150 mL)

Sources & evidence

ORD record
ord-8b4ee6d9cc88456ca134635233d0a925
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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