Ammonium Chloride → 2-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinamine

HRID 527552Notes

Reaction equation

HRID 527552 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6]2[C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][N:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Cl-].[NH4+]>[Fe].O1CCCC1.O>[CH3:1][C:2]1([CH3:21])[C:6]2[C:7]([O:11][C:12]3[N:13]=[CH:14][C:15]([NH2:18])=[CH:16][N:17]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 679586942-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-nitropyrimidine2×

Product 1

HCID 679585232-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinamineYield 68.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-nitropyrimidine (Intermediate 64, 1.257 g) in a mixture tetrahydrofuran/water (30 ml/15.00 ml) iron (1.222 g, 21.88 mmol) and ammonium chloride (1.170 g, 21.88 mmol) were added. The reaction mixture was stirred at room temperature for 48 hours. The catalyst was filtered off, and the filtrate was extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over sodium sulphate, filtered and evaporated. The residue was recrystallized from ethyl acetate to afford the title compound (768 mg) as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. extractionthe filtrate was extracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bf817dcfa925476692a0d8586b6d5c05
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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