4-Chlorothieno[3,2-d]pyrimidine → 4-(1H-pyrazol-4-yl)-3-(1-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl)-1H-isochromen-1-one hydrochloride

HRID 634472Notes

Reaction equation

HRID 634472 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:6]1[O:7][C:8](=[O:21])[C:9]2[C:14]([C:15]=1[C:16]1[CH:17]=[N:18][NH:19][CH:20]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:5].[Cl:22][C:23]1[C:24]2[S:31][CH:30]=[CH:29][C:25]=2[N:26]=[CH:27][N:28]=1>CC(O)(C)C>[ClH:22].[NH:18]1[CH:17]=[C:16]([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:21])[O:7][C:6]=2[CH:4]([NH:3][C:23]2[C:24]3[S:31][CH:30]=[CH:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH3:5])[CH:20]=[N:19]1

Participants

4

Reactant 2

HCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 1181310403-(1-aminoethyl)-4-(1H-pyrazol-4-yl)-1H-isochromen-1-one dihydrochloride2×

Product 1

HCID 1181314794-(1H-pyrazol-4-yl)-3-(1-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl)-1H-isochromen-1-one hydrochlorideYield 29.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3-(1-aminoethyl)-4-(1H-pyrazol-4-yl)-1H-isochromen-1-one dihydrochloride (Intermediate E4, 62 mg, 0.189 mmol), 4-chlorothieno[3,2-d]pyrimidine (45.1 mg, 0.264 mmol), TEA (0.092 ml, 0.661 mmol) were reacted in t-BuOH (1.1 ml) at 85° C. for 2 hrs and 90° C. for 4 hrs. The reaction was quenched by the addition of 1M HClaqueous (2 ml) and purified via reverse phase chromatography using a Biotage C18 60 g SNAP with a gradient of water and acetonitrile to give the title compound (24 mg, 29.8%) as yellowish solid.

Workup

  1. customThe reaction was quenched by the addition of 1M HClaqueous (2 ml)
  2. custompurified via reverse phase chromatography

Sources & evidence

ORD record
ord-92997b86301f46cd8627b83a01802d52
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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