Hydrochloric Acid → 6-(aminomethyl)-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022502Notes

Reaction equation

HRID 1022502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]#[N:19])[CH:14]=2)[N:9]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]1=[O:26].Cl.[OH-].[Na+]>C1COCC1.C(Cl)Cl>[NH2:19][CH2:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:8](=[O:26])[N:7]([CH2:6][C:5]1[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:16]2=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49764534HCID 49764534, compound

Product 1

HCID 667329246-(aminomethyl)-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dioneYield 41.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 0.55 g of the compound obtained in Step 12.1, and 2.94 ml of a 2M borane/dimethyl sulfide complex in THF, in 15 ml of THF is irradiated in a microwave field for 1 minute at 100° C. The reaction medium is taken up in DCM. 50 ml of 1N HCl are added and the mixture is stirred for 2 hours at room temperature. The resulting mixture is neutralized with 2N sodium hydroxide solution. This resulting mixture is extracted with DCM, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on an RP18 column, eluting with a water/ACN mixture from (90/10, v/v) to (50/50, v/v) to give 0.23 g of the expected product.

Workup

  1. extractionThis resulting mixture is extracted with DCM
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue is chromatographed on an RP18 column
  6. washeluting with a water/ACN mixture from (90/10

Sources & evidence

ORD record
ord-af764bba74e7421c9be7b7a2cb32a6ca
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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