Chloroacetaldehyde → 7-Deazaguanine

HRID 417831

反応式

HRID 417831 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([OH:9])[N:3]=1.Cl[CH2:11][CH:12]=O.C([O-])(=O)C.[Na+].CN(C=O)C>O>[NH2:1][C:2]1[NH:3][C:4](=[O:9])[C:5]2[CH:12]=[CH:11][NH:8][C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 33ChloroacetaldehydeHCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 178507952HCID 178507952、化合物

生成物 1

HCID 1354087147-Deazaguanine収率 52.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2,4-diamino-6-hydroxypyrimidine (300 g, 2.37 mol), chloroacetaldehyde (50% aq. solution, 382 g, 2.43 mol, 303 mL, 1.02 eq.), sodium acetate (195 g, 2.37 mol), DMF (2.5 L), and water (360 mL) was stirred mechanically at rt for 2 days. The resulting solid was collected by filtration, and washed with water (50 mL×3). The mother liquor was concentrated to give additional material which was washed with water (50 mL×3). The combined solid materials were recrystallized from MeOH to give the title compound as a white powder (186 g, 52% yield, HPLC purity: 100%). tR: 2.21 min. 1H-NMR (DMSO-d6) δ 11.00 (br. s, 1H), 10.33 (br. s, 1H), 6.63 (q, 1H), 6.21 (q, 1H), 6.12 (br. s, 2H).

後処理

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water (50 mL×3)
  3. concentrationThe mother liquor was concentrated
  4. customto give additional material which
  5. washwas washed with water (50 mL×3)
  6. customThe combined solid materials were recrystallized from MeOH

出典と根拠

ORDレコード
ord-23902cc87e30426b81b1d0c7c2438a8f
出典データセット
uspto-grants-2012_01
特許番号
US08093229B2

関連ノート

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