Sodium → HCID 21467991、化合物

HRID 54280

反応式

HRID 54280 の反応式
[Na].[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6](I)=[C:5]([CH3:11])[N:4]=1.[CH3:12][C:13]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)([CH3:19])/[CH:14]=[CH:15]/B(O)O>C(O)C>[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6](/[CH:15]=[CH:14]/[C:13]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=2)([CH3:12])[CH3:19])=[C:5]([CH3:11])[N:4]=1

参加物

5

反応物 3

HCID 5360545SodiumHCID 158557925-Iodo-6-methylpyrimidine-2,4-diamineHCID 21468004trans-3-Methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid

生成物 1

HCID 21467991HCID 21467991、化合物収率 56.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

Sodium metal, 4.1 grams (0.18 mole), was stirred with 250 mL of ethanol for 30 minutes. After this time 20.0 grams (0.08 mole) of 2,4-diamino-5-iodo-6-methylpyrimidine (prepared in Step B of Example 3), 27.6 grams (0.11 mole) of trans-3-methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid, and 9.2 grams (0.008 mole) of tetrakistriphenylphosphine palladium(0) were added. The reaction mixture was purged with nitrogen, and then heated to 80° C. where it stirred for about 28 hours. After this time the reaction mixture was concentrated under reduced pressure to about 20% of the original volume and then poured into 300 mL of water. The mixture was cooled in an ice-bath, and a solid was collected by filtration. The solid was triturated with a mixture of 1:1 petroleum ether:diethyl ether, and then subjected to column chromatography on silica gel using 5% methanol in methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure to a solid residue. The solid was recrystallized from 1-propanol and water, yielding 15.2 grams of trans-2,4-diamino-6-methyl-5-[3-(4-trifluoromethylphenyl)-3-methyl-1-butenyl]pyrimidine, mp 182°-185° C. The NMR spectrum was consistent with the proposed structure.

後処理

  1. customThe reaction mixture was purged with nitrogen
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to about 20% of the original volume
  3. additionpoured into 300 mL of water
  4. temperatureThe mixture was cooled in an ice-bath
  5. filtrationa solid was collected by filtration
  6. customThe solid was triturated with a mixture of 1:1 petroleum ether
  7. concentrationconcentrated under reduced pressure to a solid residue
  8. customThe solid was recrystallized from 1-propanol and water

出典と根拠

ORDレコード
ord-70aa6cbdaa024f8fb5516b67c593101f
出典データセット
uspto-grants-1997_04
特許番号
US05622954

関連ノート

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