Ammonia → 2-(3-Chloroanilino)4-[1-(2-acetamidoethyl)imidazol-5-yl]pyrimidine

HRID 1064319Notes

Reaction equation

HRID 1064319 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[N:17]=2)=[CH:14][N:13]=[CH:12]1.N>N1C=CC=CC=1.CCOC(C)=O>[Cl:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[NH:22][C:18]1[N:17]=[C:16]([C:15]2[N:11]([CH2:10][CH2:9][NH:8][C:5](=[O:7])[CH3:6])[CH:12]=[N:13][CH:14]=2)[CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 222734814-[1-(2-Aminoethyl)imidazol-5-yl]-2-(3-chloroanilino)pyrimidine

Product 1

HCID 222735332-(3-Chloroanilino)4-[1-(2-acetamidoethyl)imidazol-5-yl]pyrimidineYield 39.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (0.58 μl, 1.0 mmol) was added to solution of 2-(3-chloroanilino)-4-[1-(2-aminoethyl)imidazol-5-yl]pyrimidine (Example 13; 0.30 g, 0.63 mmol) in pyridine (2 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 2 hours. 7M Methanolic ammonia (0.5 ml) was added and the mixture diluted with EtOAc (10 ml). The precipitate was removed by filtration and the filtrate pre-absorbed on to silica gel and purified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (11:1) to give the title compound (88 mg, 39%) as a white solid. NMR 9.68 (s, 1H), 8.43 (d, 1H), 8.03-7.96 (m, 2H), 7.81 (s, 1H), 7.79 (s, 1H), 7.60 (dd, 1H), 7.33 (t, 1H), 7.12 (d, 1H), 6.98 (dd, 1H), 4.56-4.46 (m, 2H), 3.44-3.37 (m, 2H), 1.80 (s, 3H); m/z 357.

Workup

  1. customThe precipitate was removed by filtration
  2. customthe filtrate pre-absorbed on to silica gel
  3. custompurified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (11:1)

Sources & evidence

ORD record
ord-2efe5ffa2a8147a0a08d2c9e2f2f3f9f
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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