Isovaleryl chloride → HCID 9886605, compound

HRID 1005722Notes

Reaction equation

HRID 1005722 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:6]=[C:7]([C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:15])[C:8]2[S:13][CH:12]=[CH:11][C:9]=2[N:10]=1.C([NH+](CC)CC)C.[C:28](Cl)(=[O:33])[CH2:29][CH:30]([CH3:32])[CH3:31]>C(Cl)Cl>[CH3:31][CH:30]([CH3:32])[CH2:29][C:28]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[N:6]=[C:7]([C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:15])[C:8]2[S:13][CH:12]=[CH:11][C:9]=2[N:10]=1)=[O:33]

Participants

5

Reactant 3

HCID 66054Isovaleryl chlorideHCID 1385867TriethylammoniumHCID 22674375[2-[(2-Aminoethyl)amino]thieno[3,2-d]pyrimidin-4-yl]-2-thienylmethanone

Product 1

HCID 9886605HCID 9886605, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-aminoethylamino)thieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (50 mg, 0.16 mmol) in CH2Cl2 (2 mL) was treated with triethylammonium methylpolystyrene carbonate (80 mg, 0.25 mmol) then isovaleryl chloride (30 mg, 0.25 mmol) and shaken at room temperature for 6 h. The reaction mixture was treated with tris-(2-aminoethyl)amine polystyrene (0.20 g, 0.75 mmol), shaken at room temperature for 16 h, treated with polystyrene methylisocyanate (0.18 g, 0.25 mmol) and CH2Cl2 (2 mL), shaken for a further 6 h then filtered and concentrated in vacuo to give the title compound (35 mg, 55%) as a yellow solid.

Workup

  1. stirringshaken for a further 6 h
  2. filtrationthen filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-055635073c274f71be04a1a74580e483
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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