Water → HCID 59755105, compound

HRID 556396Notes

Reaction equation

HRID 556396 reaction equation
[NH2:1][C:2]1[C:10]2[C:9]([CH3:11])=[N:8][C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=3)=[N:6][C:5]=2[S:4][C:3]=1[C:22]([NH2:24])=[O:23].[O:25]=[C:26](Cl)OC(Cl)(Cl)Cl.O>O1CCOCC1>[CH3:11][C:9]1[C:10]2[C:2]3[NH:1][C:26](=[O:25])[NH:24][C:22](=[O:23])[C:3]=3[S:4][C:5]=2[N:6]=[C:7]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=2)[N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 57503713HCID 57503713, compound

Product 1

HCID 59755105HCID 59755105, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g (3 mmol) 5-amino-4-methyl-2-(4-iso-propoxy-phenyl)-thieno[2,3-d]pyrimidine-6-carboxamide was suspended in 200 ml dioxane, and following the addition of 0.73 ml (6 mmol) diphosgene the suspension is refluxed for 2 h. Having cooled down to room temperature, 20 ml water was carefully added and the precipitate was subsequently sucked off. 0.8 g (68%) 9-methyl-7-(4-iso-propoxy-phenyl)-thieno[2,3-d:4,5-d′]-dipyrimidine-2,4(1H,3H)-dione is obtained.

Workup

  1. temperatureis refluxed for 2 h

Sources & evidence

ORD record
ord-1aceefbe771441d2b55cecf9ea4db1e6
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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