Formaldehyde → 7-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

HRID 533211ノート

反応式

HRID 533211 の反応式
[NH2:1][C@@H:2]1[CH2:8][O:7]C(C)(C)[O:5][CH2:4][C@H:3]1[OH:11].[CH:12]1[C:16]2[N:17]=[CH:18][NH:19][C:20](=[O:21])[C:15]=2[NH:14][CH:13]=1.[CH2:22]=O>O>[OH:7][CH2:8][CH:2]([NH:1][CH2:22][C:12]1[C:16]2[N:17]=[CH:18][NH:19][C:20](=[O:21])[C:15]=2[NH:14][CH:13]=1)[CH:3]([OH:11])[CH2:4][OH:5]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 58287017(5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-olHCID 1354888819-Deazahypoxanthine

生成物 1

HCID 1360362067-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one収率 30%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

A mixture of (5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol (155 mg, 0.96 mmol), 9-deazahypoxanthine (100 mg, 0.74 mmol) and 37% aq formaldehyde (140 μl, 1.85 mmol) in water (2 ml) was stirred and heated in stoppered flask at 85° C. overnight. The solution was evaporated to dryness. The residue was stirred in methanolic ammonia for 10 minutes and then evaporated. The residue was chromatographed on silica (DCM-MeOH-cNH3 6:3.5:0.5) to give the racemic 7-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (55 mg, 0.20 mmol, 30% yield) as a white solid 1H NMR (CDCl3) 2.76 (1H, q, J 5.2 Hz), 3.48 (1H, dd, J 6.3, 11.9 Hz), 3.60 (2H, m), 3.70 (2H, m), 3.85 (2H, ABq), 7.34 (1H, s), 7.78 (1H, s). 13C NMR (CDCl3) δ0.2, 59.8, 59.8, 63.5, 71.2, 113.1, 117.5, 129.2, 142.4, 143.5, 155.4. m/z (ESI+) 537 (2MH+, 20%), 269 (MH+, 100%). HRMS (ESI+) C11H16N4O4 requires 269.1241. found 269.1250.

後処理

  1. customThe solution was evaporated to dryness
  2. stirringThe residue was stirred in methanolic ammonia for 10 minutes
  3. customevaporated
  4. customThe residue was chromatographed on silica (DCM-MeOH-cNH3 6:3.5:0.5)

出典と根拠

ORDレコード
ord-efabb7a3f7d94350b9bbf38e43efa91d
出典データセット
uspto-grants-2014_10
特許番号
US08853224B2

反応ノート

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