2,4,5-Trichloropyrimidine → Phenylglycine nitrile

HRID 1041260Notes

Reaction equation

HRID 1041260 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1>CCOC(C)=O>[Cl:11][C:12]1[N:17]=[C:16]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=2)[C:15]([Cl:19])=[CH:14][N:13]=1.[NH2:13][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[CH2:8][C:9]#[N:10]

Participants

5

Reactant 2

HCID 2372592,4,5-TrichloropyrimidineHCID 4847850(3-Amino-phenyl)-acetonitrile

Product 2

HCID 76307Phenylglycine nitrileHCID 86633979[3-(2,5-Dichloro-pyrimidin-4-ylamino)-phenyl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Example 1229b [3-(2,5-Dichloro-pyrimidin-4-ylamino)-phenyl]-acetonitrile was prepared from (3-Amino-phenyl)-acetonitrile and 2,4,5-Trichloro-pyrimidine in an analogous manner to Example 1223b. Title product was isolated as a beige solid (144 mg, 40%) after silica gel chromatography (ISCO 40 g 0-100% EtOAc in hexanes). 91% HPLC purity, MP=155-157, LCMS 279.11 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.26 (s, 1H), 7.66 (d, J=8.6 Hz, 2H), 7.45 (dd, J=7.8 Hz, 1H), 7.28 (d, J=8.6 Hz, 1H), 7.17 (d, J=7.5 Hz, 1H), 3.82, s, 1H).

Sources & evidence

ORD record
ord-fbb58764c9594073a04b38973f212c59
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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