Dimethylformamide → 1-(4-Fluorophenoxy)-3-[2-(1,3,5-trimethylpyrimidine-2,4-dion-6-ylamino)-ethylamino]-propan-2-ol hydrogen fumarate

HRID 365190

反応式

HRID 365190 の反応式
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH:2]1O[CH2:3]1.[NH2:13][CH2:14][CH2:15][NH:16][C:17]1[N:18]([CH3:27])[C:19](=[O:26])[N:20]([CH3:25])[C:21](=[O:24])[C:22]=1[CH3:23].CN(C)C=O.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>C(O)C.C(OCC)(=O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([O:38][CH:2]([CH2:3][NH:13][CH2:14][CH2:15][NH:16][C:17]1[N:18]([CH3:27])[C:19](=[O:26])[N:20]([CH3:25])[C:21](=[O:24])[C:22]=1[CH3:23])[CH2:1][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:37]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 444972Fumaric AcidHCID 27247922-[(4-Fluorophenoxy)methyl]oxiraneHCID 128188664-(2-aminoethylamino)-1,3,5-trimethylpyrimidine-2,6(1H,3H)-dione

生成物 1

HCID 704540321-(4-Fluorophenoxy)-3-[2-(1,3,5-trimethylpyrimidine-2,4-dion-6-ylamino)-ethylamino]-propan-2-ol hydrogen fumarate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3.36 g. 4-Fluorophenyl glycidyl ether and 8.5 g. 4-(2-aminoethylamino)-1,3,5-trimethylpyrimidine-2,6-(1H,3H)-dione are dissolved in 10 ml. dimethylformamide and left to stand for 2 days at ambient temperature. The reaction mixture is then poured into 100 ml. water, extracted with methylene chloride, dried and evaporated. The viscous oil obtained is separated by column chromatography using silica gel and, as elution agent, methylene chloride-ammonia-saturated methanol (20:1 v/v). The product obtained by evaporation of the pure fractions is dissolved in 20 ml. ethyl acetate, whereafter 1.8 g. fumaric acid, dissolved in ethanol, is added thereto. After filtering off with suction, the crystalline product obtained is recrystallized from ethanol, with the addition of 0.9 g. fumaric acid and with the use of active charcoal. There are obtained 5.2 g. (52% of theory) of the desired product in the form of colorless crystals; m.p. 163°-167° C.

後処理

  1. additionThe reaction mixture is then poured into 100 ml
  2. extractionwater, extracted with methylene chloride
  3. customdried
  4. customevaporated
  5. customThe viscous oil obtained
  6. customis separated by column chromatography
  7. washas elution agent, methylene chloride-ammonia-saturated methanol (20:1 v/v)
  8. customThe product obtained by evaporation of the pure fractions
  9. dissolutionis dissolved in 20 ml
  10. additionis added
  11. filtrationAfter filtering off with suction
  12. customthe crystalline product obtained
  13. customis recrystallized from ethanol, with the addition of 0.9 g
  14. customThere are obtained 5.2 g

出典と根拠

ORDレコード
ord-cec10090afb14f8d95a58242ddb2d449
出典データセット
uspto-grants-1986_08
特許番号
US04608383

関連ノート

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