tert-Butanol → HCID 21995254、化合物

反応式

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.C([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)[N:29]=1)(O)=O.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[C:47]([O:51][C:23]([NH:20][C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]2[CH:36]=[C:37]([O:45][CH3:46])[C:38]([O:43][CH3:44])=[C:39]([O:41][CH3:42])[CH:40]=2)[N:29]=1)=[O:8])([CH3:50])([CH3:49])[CH3:48]

参加物

反応物 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 21995247HCID 21995247、化合物

生成物 1

HCID 21995254HCID 21995254、化合物

実験手順

To a solution of diphenylphosphorylazide (0.92 ml, 4.3 mmol) in tertbutyl alcohol (10 ml), was added triethylamine (1,2 ml, 8.5 mmol) and 4-carboxy-N-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine (1.0 g, 2.9 mmol), [see Example 121] and the mixture heated at reflux for 2 h. After this time the solvent was evaporated and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with water (100 ml), dried (MgSO4) and concentrated under reduced pressure. Column chromatography [silica 2% methanol CH2Cl2 ] gave the title compound (850 mg) as a light yellow solid m.p. 124°. δH (CDCl3) 8.27 (1H, d, J 5.8 Hz), 7.45 (1H, br s), 7.32 (1H, d, J 5.8 Hz), 7.20 (1H, br s), 6.81 (2H, s), 3.85 (6H, s), 3.81 (3H, s) and 1.53 (9H, s). MS m/z 377 (M+H)+.