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Sodium Iodide → 1-(4-(5-Fluoro-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)butyl)-5-(thiophen-2-yl)pyrimidine-2,4(1h,3h)-dione hydrochloride

HRID 1661078
Notes
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Reaction equation

HRID 1661078 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:9](=[O:17])[NH:8][C:7]1=[O:18].Cl.[F:20][C:21]1[CH:22]=[C:23]2[C:31](=[CH:32][CH:33]=1)[C:26]1([CH2:30][CH2:29][NH:28][CH2:27]1)[CH2:25][CH2:24]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN1C(=O)CCC1>[ClH:1].[F:20][C:21]1[CH:22]=[C:23]2[C:31](=[CH:32][CH:33]=1)[C:26]1([CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[CH:11]=[C:10]([C:12]4[S:13][CH:14]=[CH:15][CH:16]=4)[C:9](=[O:17])[NH:8][C:7]3=[O:18])[CH2:27]1)[CH2:25][CH2:24]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 592339261-(4-chlorobutyl)-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dioneHCID 674294815-Fluoro-2,3-dihydrospiro[indene-1,3'-pyrrolidine]hydrochloride salt

Product 1

HCID 674283101-(4-(5-Fluoro-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)butyl)-5-(thiophen-2-yl)pyrimidine-2,4(1h,3h)-dione hydrochloride
Yield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(4-chlorobutyl)-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione (Prep23, 50 mg, 0.18 mmol), 5-fluoro-2,3-dihydrospiro[indene-1,3′-pyrrolidine]hydrochloride salt (Prep14, 50 mg, 0.26 mmol), potassium carbonate (108 mg, 0.78 mmol), sodium iodide (108 mg, 0.72 mmol) and NMP (1 ml) was stirred at 70° C. overnight. The mixture was then diluted with water and extracted with ethyl acetate. The EA phase was evaporated and the crude purified by preparative TLC to give the free base of the title compound (72 mg). The compound was purified by preparative HPLC and treated with a 1N solution of HCl-ether and freeze-dried to give the title compound (30 mg, y=35%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe EA phase was evaporated
  3. customthe crude purified by preparative TLC

Sources & evidence

ORD record
ord-566d3ed1310d493cab32b7a8ecfc67f9
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030322B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes