Dimethylformamide → 5-(5-Iodo-2-isopropyl-4-methoxyphenoxy)pyrimidine-2,4-diamine

HRID 18673

反応式

HRID 18673 の反応式
[I:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([CH:20]([CH3:22])[CH3:21])=[C:6]([CH:19]=1)[O:7][C:8](=[CH:11]NC1C=CC=CC=1)[C:9]#[N:10].C(=O)(O)O.[NH2:29][C:30]([NH2:32])=[NH:31].CN(C=O)C.C(OCC)(=O)C>O>[I:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([CH:20]([CH3:22])[CH3:21])=[C:6]([CH:19]=1)[O:7][C:8]1[C:9]([NH2:10])=[N:31][C:30]([NH2:32])=[N:29][CH:11]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 286947Carbonic acid-guanidine (1:1)HCID 674237962-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-3-phenylamino-acrylonitrile

生成物 1

HCID 159538025-(5-Iodo-2-isopropyl-4-methoxyphenoxy)pyrimidine-2,4-diamine収率 99.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A solution of 2-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-3-phenylamino-acrylonitrile (280 g, 0.64 mol), guanidine carbonate (110 g, 0.61 mol), and 560 ml of DMF was heated to 120° C. for 18 hours. After cooling the mixture to 60° C., 140 ml of ethyl acetate was added. Water (1.12 L) was then added to the mixture at a rate to maintain an internal temperature of 50° C. The resulting slurry was cooled to 20° C. and aged. Precipitated solids were collected by filtration, washed with water (300 ml) followed by isopropanol (500 ml), and dried in a vacuum oven (50° C., 24 inches Hg) to give 242 g of 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine, 94% yield: m.p. 204.4-205.9 degrees C.; 1HNMR (DMSO) δ=1.2 (d, 6H), 3.3 (m, 1H), 3.8 (s, 3H), 5.85 (s, 2H), 6.4 (s, 2H), 6.9 (d, 2H), 7.35 (s, 1H)

後処理

  1. temperatureto maintain an internal temperature of 50° C
  2. temperatureThe resulting slurry was cooled to 20° C.
  3. customPrecipitated solids
  4. filtrationwere collected by filtration
  5. washwashed with water (300 ml)
  6. customdried in a vacuum oven (50° C., 24 inches Hg)

出典と根拠

ORDレコード
ord-ce7a1d4f6b89469cbe098ff9fbce3425
出典データセット
uspto-grants-2010_06
特許番号
US07741484B2

関連ノート

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