Allyl isocyanate → HCID 9930157, compound

HRID 1005723Notes

Reaction equation

HRID 1005723 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.[CH2:21]([N:24]=[C:25]=[O:26])[CH:22]=[CH2:23]>CN(C=O)C>[CH2:21]([NH:24][C:25]([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:26])[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 15123Allyl isocyanateHCID 22674375[2-[(2-Aminoethyl)amino]thieno[3,2-d]pyrimidin-4-yl]-2-thienylmethanone

Product 1

HCID 9930157HCID 9930157, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(2-aminoethylamino)thieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (50 mg, 0.16 mmol) in anhydrous DMF (1 mL) was treated with allyl isocyanate (21 mg, 0.25 mmol), shaken at room temperature for 4 h, treated with tris-(2-aminoethyl)amine polystyrene (0.20 g, 0.75 mmol), shaken at 35° C. for 16 h, treated with polystyrene methylisocyanate (0.22 g, 0.32 mmol) and DMF (2 mL) and shaken for a further 6 h. The reaction mixture was filtered and concentrated in vacuo to give the title compound (55 mg, 86%) as a yellow solid.

Workup

  1. stirringshaken at 35° C. for 16 h
  2. stirringshaken for a further 6 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e873ab24b68d43a88e9200078b8508e7
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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