Water → N-[(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 338143Notes

Reaction equation

HRID 338143 reaction equation
CN(C)C(N(C)C)=N.[C:9]1([C@:15]23[CH2:23][NH:22][CH2:21][C@H:20]2[CH2:19][S:18][C:17]([NH:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:16]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:33][C:34]1[CH:35]=[N:36][C:37](Cl)=[N:38][CH:39]=1.O>CS(C)=O>[F:33][C:34]1[CH:35]=[N:36][C:37]([N:22]2[CH2:21][C@@H:20]3[C@@:15]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)([N:16]=[C:17]([NH:24][C:25](=[O:32])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[S:18][CH2:19]3)[CH2:23]2)=[N:38][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 664601,1,3,3-TetramethylguanidineHCID 5834662-Chloro-5-fluoropyrimidineHCID 86762229N-[(4aR,7aS)-7a-Phenyl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Product 1

HCID 86762233N-[(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

N,N,N′,N′-tetramethylguanidine (3.4 mL, 27 mmol) is added to a solution of N-[(4aR,7aS)-7a-phenyl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (7.5 g, 22 mmol) and 5-fluoro-2-chloropyrimidine (3.5 g, 27 mmol) in dimethylsulfoxide (75 mL). The reaction is stirred at 100° C. for 2 hours, cooled to room temperature and water is added (225 mL). The precipitated product is isolated by filtration and is dried in a vacuum oven at 45° C. to give the title compound (9.5 g, 99%). ES/MS (m/e): 434 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. customThe precipitated product is isolated by filtration
  3. customis dried in a vacuum oven at 45° C.

Sources & evidence

ORD record
ord-0b70ede07d8f4eb29cb341a59ca22cc1
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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