2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide

Base Information

• Chemical Name: 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide
• CAS No.: 1388894-17-4
• Molecular Formula: C₂₁H₂₈N₄O₃S
• Molecular Weight: 416.544

Synonyms:2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide

Chemical Property of 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide

Chemical Property:

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Technology Process of 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide

There total 8 articles about 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C21H27N3O4S (1388894-16-3) → 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide (1388894-17-4)

Guidance literature:

With dmap; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

Reference yield:

(1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol (1228947-14-5) → 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide (1388894-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 3 h / 60 °C / Inert atmosphere

2.1: hydrogenchloride / dichloromethane / Cooling with ice

3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 24 h / 20 °C

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium chloride / N,N-dimethyl-formamide / 24 h / 20 °C

With hydrogenchloride; dmap; dipyridinium dichromate; sodium hydride; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate (1029689-54-0) → 2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide (1388894-17-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 20 - 180 °C / Inert atmosphere

1.2: Cooling with ice

2.1: trichlorophosphate / 20 - 110 °C

3.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / -30 °C / Inert atmosphere

4.1: CHIRALPAK IA / carbon dioxide; methanol / Resolution of racemate

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

6.2: 3 h / 60 °C / Inert atmosphere

7.1: hydrogenchloride / dichloromethane / Cooling with ice

8.1: dipyridinium dichromate / N,N-dimethyl-formamide / 24 h / 20 °C

9.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium chloride / N,N-dimethyl-formamide / 24 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; dipyridinium dichromate; sodium hydride; diisobutylaluminium hydride; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; carbon dioxide; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

(1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol

ethyl 2-[12-hydroxy-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]acetate

ethyl 2-[12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]acetate

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