Acetic Acid → 5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine

HRID 81821Notes

Reaction equation

HRID 81821 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:18]=2)[C:15]([NH2:17])=[S:16])=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH3:29][C:30](O)=O>C(OC(OCC)CBr)C.CC1C=CC(S(O)(=O)=O)=CC=1>[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([C:15]2[S:16][CH:29]=[CH:30][N:17]=2)=[CH:18][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]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 595986045-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide

Product 1

HCID 595986595-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamineYield 28%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 74852Ethane, 2-bromo-1,1-diethoxy-Catalyst

Conditions

Temperature
110 °C

Procedure

To a solution of 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide (0.23 g, 0.69 mmol) in HOAc (5 ml) was added bromoactaldehyde diethylacetal (0.18 g, 0.9 mmol) and TsOH (5 mg) as a catalyst. The reaction mixture was heated at 110° C. for 16 hrs and basified with sat. NaHCO3 solution. The aqueous solution was extracted into methylene chloride. The combined organic extract was dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (5% MeOH in methylene chloride with 1% NH4OH) gave 5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine (0.070 g, 28%) as a yellow solid. (M+H)=358

Workup

  1. extractionThe aqueous solution was extracted into methylene chloride
  2. extractionThe combined organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8910f0e17a534a98b4ba125cd9463906
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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