Sodium Hydroxide → 5-(2-Isopropyl-4-methoxy-5-pyrrol-1-yl-phenoxy)-pyrimidine-2,4-diamine

HRID 38368Notes

Reaction equation

HRID 38368 reaction equation
[NH2:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.COC1[CH:29]=[CH:28][C:27](OC)=[CH:26]O1.[OH-].[Na+]>CC(O)=O>[CH:17]([C:5]1[CH:4]=[C:3]([O:20][CH3:21])[C:2]([N:1]2[CH:29]=[CH:28][CH:27]=[CH:26]2)=[CH:16][C:6]=1[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 595985735-(5-Amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamineHCID 670534482,5-Dimethoxypyran

Product 1

HCID 595987615-(2-Isopropyl-4-methoxy-5-pyrrol-1-yl-phenoxy)-pyrimidine-2,4-diamineYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(5-amino-2-Isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.303 g, 1.0 mmol) in 15 mL AcOH was added 2,5-dimethoxypyran (0.152 g, 1.2 mmol). The solution was warmed to reflux. After 2 h the solution was cooled and poured over ice/H2O. The solution was converted to pH=8 with 50% NaOH and extracted with ethyl acetate (3×75 mL). The combined organics were washed with H2O, washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to give a brown solid. Purification via flash chromatography (CH2Cl2/MeOH 97:3) afforded 5-(2-isopropyl-4-methoxy-5-pyrrol-1-yl-phenoxy)-pyrimidine-2,4-diamine (0.244 g, 72%) as a pale yellow solid. (M+H)=340.

Workup

  1. temperatureThe solution was warmed to reflux
  2. temperatureAfter 2 h the solution was cooled
  3. extractionextracted with ethyl acetate (3×75 mL)
  4. washThe combined organics were washed with H2O
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown solid
  10. customPurification via flash chromatography (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-0be3b8b1423548bc992818414f2de63a
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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