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

Potassium Carbonate → 5-(5-Iodo-2-isopropyl-4-prop-2-ynyloxy-phenoxy)-pyrimidine-2,4-diamine

HRID 38388
Notes
Print preview

Reaction equation

HRID 38388 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:13]([OH:19])=[C:12]([I:20])[CH:11]=2)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Cl)[C:28]#[CH:29]>CN(C)C=O>[I:20][C:12]1[C:13]([O:19][CH2:29][C:28]#[CH:27])=[CH:14][C:15]([CH:16]([CH3:18])[CH3:17])=[C:10]([CH:11]=1)[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 159538644-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol

Product 1

HCID 595987185-(5-Iodo-2-isopropyl-4-prop-2-ynyloxy-phenoxy)-pyrimidine-2,4-diamineYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

To 4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol (200 mg, 0.43 mmol) dissolved in anhydrous N,N-dimethylformamide (2 mL) was added anhydrous potassium carbonate (414 mg, 3.00 mmol) and propargyl chloride (0.03 mL, 0.43 mmol). After stirring at room temperature overnight, the reaction was extracted with dichloromethane, water and brine. The dichloromethane layer was dried using anhydrous magnesium sulfate, concentrated, and purified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide) to yield 5-(5-iodo-2-isopropyl-4-prop-2-ynyloxy-phenoxy)-pyrimidine-2,4-diamine as white solid (131 mg, 71%), MS (M+H)=425.

Workup

  1. extractionthe reaction was extracted with dichloromethane, water and brine
  2. dry with materialThe dichloromethane layer was dried
  3. concentrationconcentrated
  4. custompurified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-083b306a62864c61b65dfa1b32c2e254
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524725B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes