Methane, dichloromethoxy- → 5-(6-Phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde

HRID 2297814Notes

Reaction equation

HRID 2297814 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[S:19][C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[CH:27](Cl)[O:28]C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[C:20]1([C:18]2[S:19][C:12]3[C:11]([NH:10][C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[NH:1][CH:2]=[C:3]5[CH:27]=[O:28])=[N:16][CH:15]=[N:14][C:13]=3[CH:17]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 9884465(1H-Indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine

Product 1

HCID 183827505-(6-Phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-Indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine (481 mg, 1.4 mmol) in 3 mL of methylene chloride in a 3-neck flask with dropping funnel under nitrogen at 0° C. was added titanium tetrachloride (461 mL, 4.2 mmol) dropwise. The mixture was stirred for 30 minutes and then dichloromethoxy methane (380 mL, 4.2 mmol) was added dropwise. The reaction was warmed to room temperature and concentrated in vacuo. The resulting residue was pre-absorbed onto silica gel (10 gm) and purified by flash chromatography using a 5% methanol/methylene chloride to afford the title compound in 92% yield. RP18-HPLC RT: 4.80 minutes; API MS: 371.20 (M+1); MP: 174-175° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was pre-absorbed onto silica gel (10 gm)
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6a287ddceffc4e7ea6c12046521ca186
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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