Dimethylformamide → 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide

反応式

[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][C:8]#[CH:9])=[O:5].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[N:31]=[C:30](Cl)[C:29]([Cl:33])=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:31]=[C:30]([NH:1][C:2]2[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=2[C:4]([NH:6][CH2:7][C:8]#[CH:9])=[O:5])[C:29]([Cl:33])=[CH:28][N:27]=1

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 2372592,4,5-Trichloropyrimidine

HCID 27644242-Amino-N-(prop-2-yn-1-yl)benzamide

生成物 1

HCID 866340252-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide収率 4%

実験手順

2-Amino-N-prop-2-ynyl-benzamide (4.20 g, 24.1 mmol) was dissolved in N,N-dimethylformamide (100 mL, 1.290 mol) and potassium carbonate (5.00 g, 36.2 mmol) was added. 2,4,5-Trichloro-pyrimidine (3.32 mL, 28.9 mmol) was added and the reaction was stirred for 48 hours. The reaction was concentrated under reduced pressure and the residue was taken up in DCM (300 mL) and washed with water (300 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-50% EtOAc/hex as the eluting solvent to obtain 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide as a pale yellow solid (298 mg, 4%). m.p.=188-191° C.; LCMS (m/e) 321 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 11.53 (s, 1H), 8.76 (d, 1H, J=8.5 Hz), 8.25 (s, 1H), 7.66-7.53 (m, 2H), 7.23-7.14 (m, 1H), 6.39 (bs, 1H), 4.34-4.25 (m, 2H), 2.34 (t, 1H, J=2.5 Hz).

後処理

concentrationThe reaction was concentrated under reduced pressure
washwashed with water (300 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by silica gel chromatography

出典と根拠

ORDレコード: ord-cfde8d8962e64d438411bf93a095cf52
出典データセット: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08552186B2

反応ノート

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