4-Aminobenzoic Acid → 4-(N-((2,4-diamino-6-pteridinyl)methyl)amino)benzoic acid

HRID 1611596

反応式

HRID 1611596 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrBr.[NH2:22][C:23]1[N:32]=[C:31]([NH2:33])[C:30]2[C:25](=[N:26][CH:27]=[C:28]([CH2:34]O)[N:29]=2)[N:24]=1.[O-2].[Ba+2].[NH2:38][C:39]1[CH:47]=[CH:46][C:42]([C:43]([OH:45])=[O:44])=[CH:41][CH:40]=1>O.CO.C(Cl)Cl.CC(N(C)C)=O>[CH:41]1[C:42]([C:43]([OH:45])=[O:44])=[CH:46][CH:47]=[C:39]([NH:38][CH2:34][C:28]2[N:29]=[C:30]3[C:31]([NH2:33])=[N:32][C:23]([NH2:22])=[N:24][C:25]3=[N:26][CH:27]=2)[CH:40]=1

参加物

10

反応物 5

HCID 9784-Aminobenzoic AcidHCID 11776TriphenylphosphineHCID 24408BromineHCID 703472,4-Diamino-6-hydroxymethylpteridineHCID 9855530Barium Oxide Nanoparticle Dispersion

生成物 1

HCID 1697484-(N-((2,4-diamino-6-pteridinyl)methyl)amino)benzoic acid収率 99%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
5 °C

実験手順

To a 2 L 3-necked round bottom flask, equipped with a dropping funnel, a thermometer, and a drying tube, were added triphenylphosphine (216 g, 0.83 mol) and anhydrous dimethylacetamide (0.66 L). The resulting clear solution was cooled to 5° C. and bromine (132 g, 0.83 mol) was added over 45 min while maintaining the temperature below 8° C. To the resulting white slurry was added 2,4-diamino-6-hydroxymethyl pteridine (53 g, 0.28 mol). The temperature rose to 35° C. due to exothermic effect. The rust colored slurry slowly dissolved over 1 h to become a dark red solution. The mixture was stirred at ambient temperature overnight (ca. 17 h) forming a dark red slurry. Barium oxide (53 g, 0.35 mol) and 4-aminobenzoic acid (57 g, 0.42 mol) were added in one portion each with vigorous stirring. The temperature rose to 70° C. due to exothermic effect and the mixture turned to a rust-colored slurry within 15 min. The reaction mixture was stirred at 55±2° C. for 24±2 h. The resulting yellow-brown slurry was cooled to 20° C., then poured into a mixture of CH2Cl2 (6.9 L) and MeOH (0.2 L). The solids were isolated by filtration, slurried in H2O (2.5 L), and the mixture was filtered again to isolate the solids. The solids were slurried in MeOH (2.5 L), isolated by filtration, and air-dried at ambient temperature, to give 85 g (99%) of crude product as a brownish-yellow powder, Lot BM-02G-54.

後処理

  1. customTo a 2 L 3-necked round bottom flask, equipped with a dropping funnel
  2. temperaturewhile maintaining the temperature below 8° C
  3. customrose to 35° C. due to exothermic effect
  4. customforming a dark red slurry
  5. customrose to 70° C. due to exothermic effect
  6. stirringThe reaction mixture was stirred at 55±2° C. for 24±2 h
  7. temperatureThe resulting yellow-brown slurry was cooled to 20° C.
  8. customThe solids were isolated by filtration
  9. filtrationthe mixture was filtered again
  10. customto isolate the solids
  11. customisolated by filtration
  12. customair-dried at ambient temperature

出典と根拠

ORDレコード
ord-8da75c23c8b5400b9ae089491ded9839
出典データセット
uspto-grants-2006_01
特許番号
US06989386B2

関連ノート

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