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

HRID 533211노트

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HRID 533211 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
85 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-efabb7a3f7d94350b9bbf38e43efa91d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853224B2

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