HCID 69056831, compound → HCID 69091873, compound

HRID 2105132Notes

Reaction equation

HRID 2105132 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH2:14][N:15]2[C:20](=[O:21])[CH2:19][CH2:18][CH2:17][C:16]2=O)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Mg]I>>[NH:1]([C:8]1[N:13]=[C:12]([CH2:14][N:15]2[CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][C:20]2=[O:21])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 69056831HCID 69056831, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 69091873HCID 69091873, compound

Procedure

By an analogous process to Method 17, 2-anilino-4-(2,6-dioxopiperidin-1-ylmethyl)pyrimidine (Method 16; 2.21 g, 7.47 mmol) was treated with methyl magnesium iodide to prepare the intermediate animal which was taken on without chromatographic purification to give the final product which was purified, after aqueous work-up, by chromatography eluting with DCM/MeOH (98:2) to give the title compound (375 mg, 17%) as a glassy solid. NMR: 1.2 (d, 3H), 1.65 (m, 2H), 1.93 (m, 2H), 2.33 (t, 2H), 3.6 (q, 1H), 4.25 (d, 1H), 4.7 (d, 1H), 6.65 (d, 1H), 6.93 (t, 1H), 7.25 (t, 2H), 7.76 (d, 2H), 8.4 (d, 1H), 9.53 (s, 1H); m/z 297.

Workup

  1. customto prepare the intermediate animal which
  2. customwas taken on without chromatographic purification

Sources & evidence

ORD record
ord-50092142ab6f4795be59e5a2fb546ea4
Source dataset
uspto-grants-2009_08
Patent number
US07579344B2

Reaction notes

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