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5-Bromopyrimidine → HCID 69550769、化合物

HRID 348554
ノート
印刷プレビュー

反応式

HRID 348554 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]1([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]2[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)C>[C:8]1([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:2]3[CH:3]=[N:4][CH:5]=[N:6][CH:7]=3)[CH2:22][CH2:21]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 783445-Bromopyrimidine2 回HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 86594093HCID 86594093、化合物

生成物 1

HCID 69550769HCID 69550769、化合物収率 20.6%

試薬・触媒・溶媒 3

HCID 1140Toluene
溶媒
HCID 3283Diethyl Ether溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

The title compound, MS (ISP): m/e=446.4 (M+H+), was prepared as for example 209, steps (A) to (C). Step (B) was performed using 5-bromo-pyrimidine as follows: A suspension of (+/−)-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-amine (1.46 g, 5.65 mmol) in toluene (35 ml) was degassed with a flow of argon for 10 minutes. Tris-(dibenzylideneacetone)dipalladium chloroform complex (179 mg, 0.17 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP, 108.0 mg, 0.17 mmol), sodium tert-butoxide (0.660 g, 6.87 mmol) and 5-bromopyrimidine (0.720 g, 4.53 mmol) were added under argon. The flask was sealed and warmed to 70° C. for 3 hours. The mixture was diluted with ethyl acetate (30 ml) and diethyl ether (30 ml) and washed three times with saturated sodium chloride solution. The organic phase was dried with sodium sulphate and evaporated, yielding a red oil. Purification was achieved by flash chromatography (dichloromethane/methanol/25% NH3 90:10:1). (+/−)-[cis-1-(2-Phenyl-cyclohexyl)-piperidin-4-yl]-pyrimidin-5-yl-amine (0.392 g, 20.6%) was obtained as an orange foam, MS (ISP): m/e=337.3 (M+H+). This was reacted with 5-methyl-isoxazole-3-carbonyl chloride in step (C).

後処理

  1. customwas degassed with a flow of argon for 10 minutes
  2. customThe flask was sealed
  3. washwashed three times with saturated sodium chloride solution
  4. dry with materialThe organic phase was dried with sodium sulphate
  5. customevaporated
  6. customyielding a red oil
  7. customPurification

出典と根拠

ORDレコード
ord-d18e491d2554494ea6062524c570b7dd
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176316B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート