Sodium Chloride → N-(2-hydroxymethyl-5-nitro-phenyl)-4-(3-pyridinyl)-2-pyrimidinamine

HRID 225497Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][N:17]=1)C=C.[Cl-].[Na+]>C1COCC1.[Cl-].[Zn+2].[Cl-]>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][N:17]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Polymethylhydrosiloxane (860 mg), tetrakis(triphenylphoshine)palladium (70 mg) and zinc chloride (2.66 mL of 0.5 M in THF, 1.33 mmol) is added to a stirred solution of N-{2-[(2-propenyloxy)-methyl]-5-nitro-phenyl}-4-(3-pyridinyl)-2-pyrmidinamine (2.60 g, 7.2 mmol) in dry THF (60 mL). The mixture is then stirred under an argon atmosphere at 30° C. for 30 h. The solvent is then evaporated off under reduced pressure to give a residue which is treated with saturated aqueous sodium chloride solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is recrystallised from THF to give the title compound as a pale-yellow crystalline solid, m.p. 247-250° C.

Workup

customThe solvent is then evaporated off under reduced pressure
customto give a residue which
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe combined extracts are dried (Na2SO4)
filtrationfiltered
customthe solvent is evaporated off under reduced pressure
customto yield the crude product which
customis recrystallised from THF

Sources & evidence

ORD record: ord-8ba30d2b424a465799786f2676ac66d9
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557105B2

Reaction notes

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