Water → HCID 22674439, compound

HRID 1005726Notes

Reaction equation

HRID 1005726 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.[OH2:21].[CH3:22][N:23]([CH:25]=[O:26])C>>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:14]([C:7]1[C:8]2[S:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:5]([NH:4][CH2:3][CH2:22][NH:23][C:25]([NH:1][CH2:2][CH2:3][NH:4][C:5]2[N:6]=[C:7]([C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)=[O:15])[C:8]3[S:13][CH:12]=[CH:11][C:9]=3[N:10]=2)=[O:26])[N:6]=1)=[O:21]

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 22674375[2-[(2-Aminoethyl)amino]thieno[3,2-d]pyrimidin-4-yl]-2-thienylmethanone2×

Product 1

HCID 22674439HCID 22674439, compoundYield 31%

Procedure

A solution of 2-(2-aminoethylamino)thieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.10 g, 0.33 mmol) in anhydrous DMF (4 mL) under argon was treated with 1,1-carbonyldiimidazole (0.05 g, 0.33 mmol), stirred for 2 h, treated with 2-(2-aminoethylamino)thieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.10 g, 0.33 mmol), stirred at room temperature for 4 h and then at 60° C. for 16 h, cooled, poured into water (25 mL) and the resulting orange suspension filtered and dried in vacuo to give the title compound (0.13 g, 31%) as an orange solid.

Workup

  1. stirringstirred at room temperature for 4 h
  2. waitat 60° C. for 16 h
  3. temperaturecooled
  4. filtrationthe resulting orange suspension filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0ed74c341a5740f89048724797dc058e
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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