HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 3-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)phenyl]-6-piperidin-1-yl-3H-thieno[3,2-d]pyrimidin-4-one

HRID 72212
Notes
Print preview

Reaction equation

HRID 72212 reaction equation
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:22][CH2:21][C@@H:20]([N:23]([CH3:25])[CH3:24])[CH2:19]4)=[CH:14][CH:13]=3)[CH:6]=[N:5][C:4]=2[CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.O>C(OCC)(=O)C>[CH3:24][N:23]([CH3:25])[C@@H:20]1[CH2:21][CH2:22][N:18]([C:15]2[CH:16]=[CH:17][C:12]([N:7]3[C:8](=[O:11])[C:9]4[S:10][C:2]([N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[CH:3][C:4]=4[N:5]=[CH:6]3)=[CH:13][CH:14]=2)[CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 689763236-Bromo-3-[4-((R)-3-dimethylaminopyrrolidin-1-yl)phenyl]-3H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 576252993-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)phenyl]-6-piperidin-1-yl-3H-thieno[3,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-3-[4-((R)-3-dimethylaminopyrrolidin-1-yl)phenyl]-3H-thieno[3,2-d]pyrimidin-4-one (40 mg) and piperidine (492 mg) was heated at 100° C. for 2 days. Water and ethyl acetate were then added, and the organic phase was washed twice with water. The ethyl acetate phase was dried over sodium sulfate and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 423.58 (C23H29N50S) was obtained in this way; MS (ESI): 424 (M+H+).

Workup

  1. washthe organic phase was washed twice with water
  2. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by preparative HPLC
  5. customThe product with the molecular weight of 423.58 (C23H29N50S) was obtained in this way

Sources & evidence

ORD record
ord-81eb96523a414840b71293a65f0edb3a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828991B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes