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(Diethylamino)sulfur trifluoride → 5-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine

HRID 925176
Notes
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Reaction equation

HRID 925176 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:16]([OH:18])[CH3:17])[CH:15]=2)=[CH:4][N:3]=1.[CH3:24]CN(S(F)(F)F)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([CH:16]=[CH2:17])=[CH:15][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22].[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([CH:16]([O:18][CH3:24])[CH3:17])=[CH:15][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 573291161-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanol

Product 2

HCID 573289585-(2-Isopropyl-4-methoxy-5-vinyl-phenoxy)-pyrimidine-2,4-diamineYield 3%HCID 595986985-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine
Yield 4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanol (1.613 g, 5.3 mmol) in 30 ml CH2Cl2 at −78° C. was added DAST (0.935 g, 5.8 mmol). After stirring 1.5 h, saturated NaHCO3 was added and the mixture was extracted by CH2Cl2. The combined organics were washed with brine and dried with Na2SO4, filtered and concentrated in vacuo. Purification via silica gel chromatography (95:5 CH2Cl2/MeOH) gave 5-(2-Isopropyl-4-methoxy-5-vinyl-phenoxy)-pyrimidine-2,4-diamine (0.044 g, 3%) as a foam ([MH]+=301) and 5-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine (0.075 g, 4%) as foam. [MH]+=303.

Workup

  1. extractionthe mixture was extracted by CH2Cl2
  2. washThe combined organics were washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-ad522038365c430e9e58da774bea8aa1
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09284279B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes