Water → 7-[(3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1054527ノート

反応式

HRID 1054527 の反応式
[N:1]([CH2:4][C@@H:5]1[C@H:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C@H:8]2[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([N:24]=[N+]=[N-])[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1)=[N+]=[N-].CP(C)C.O>C1COCC1>[NH2:1][CH2:4][C@@H:5]1[C@H:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C@H:8]2[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH2:24])[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1

参加物

5

反応物 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 867057467-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-4-azido-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 678180027-[(3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

7-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-4-azido-7H-pyrrolo[2,3-d]pyrimidine (3.933 g, 11.1 mmol) was dissolved in THF (20 ml) and trimethylphosphane (1M in THF) (44.3 ml, 44.3 mmol) was added at r.t. under N2 and the reaction stirred overnight. Water (4 ml) was added and the reaction was left for 15 mins. The solvents were removed in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% DCM to 20% 2M NH3 in MeOH:80% DCM as eluent to give the product as pale yellow foam (2.706 g, 81%): MS (ESI+) for C15H21N5O2 m/z 304.2 [M+H]+, 326.1 [M+Na]+; LCMS: Compound in solvent front; 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.27 (d, J=3.63 Hz, 1H), 6.63 (d, J=3.63 Hz, 1H), 5.02 (dt, J=12.14, 6.23 Hz, 1H), 4.92-4.99 (m, 1H), 4.48-4.61 (m, 1H), 2.82-2.91 (m, 1H), 2.71-2.82 (m, 1H), 2.40 (dt, J=12.65, 6.52 Hz, 1H), 2.27 (m, 1H), 2.04 (q, J=12.14 Hz, 1H), 1.56 (s, 3H), 1.31 (s, 3H).

後処理

  1. waitthe reaction was left for 15 mins
  2. customThe solvents were removed in vacuo
  3. customto give the crude product
  4. customThe product was purified by silica flash column chromatography

出典と根拠

ORDレコード
ord-8e850b2b2956450e85e2ce34302779b9
出典データセット
uspto-grants-2016_07
特許番号
US09394310B2

反応ノート

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