Veratrylamine → N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine

HRID 32519

Reaction equation

HRID 32519 reaction equation
[N:1]1[C:6]2[S:7][C:8]([CH:10]=O)=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][NH2:18]>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][N:18]=[CH:10][C:8]1[S:7][C:6]2[N:1]=[CH:2][N:3]=[CH:4][C:5]=2[CH:9]=1

Participants

4

Reactant 2

HCID 79832VeratrylamineHCID 17965793Thieno[2,3-d]pyrimidine-6-carbaldehyde2×

Product 1

HCID 17965764N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thieno[2,3-d]pyrimidine-6-carbaldehyde (intermediate 13) (40 mg), 3,4-dimethoxybenzylamine (0.04 ml) and 4 Å molecular sieves (150 mg) were heated at reflux in DCM (5 ml) for 3 hours under an inert atmosphere. The molecular sieves were removed by filtration and the solvent evaporated to afford the title compound as a pale yellow solid (76 mg, 100%);

Workup

  1. customThe molecular sieves were removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-36c3d37e854a49d39ca2623aeea01899
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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