Acetyl chloride → 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-propane-1,3-diol

HRID 533201ノート

反応式

HRID 533201 の反応式
C(Cl)(=O)C.[NH2:5][CH:6]([CH2:9][OH:10])[CH2:7][OH:8].[CH2:11]([O:18][CH2:19][N:20]1[C:28]2[C:27]([O:29][CH3:30])=[N:26][CH:25]=[N:24][C:23]=2[C:22]([CH:31]=O)=[CH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([BH3-])#N.[Na+]>CO>[CH2:11]([O:18][CH2:19][N:20]1[C:28]2[C:27]([O:29][CH3:30])=[N:26][CH:25]=[N:24][C:23]=2[C:22]([CH2:31][NH:5][CH:6]([CH2:9][OH:10])[CH2:7][OH:8])=[CH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 6367Acetyl chlorideHCID 68294SerinolHCID 5003444Sodium cyanoborohydrideHCID 577250835-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde

生成物 1

HCID 252231892-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-propane-1,3-diol収率 77%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Acetyl chloride (0.117 ml, 1.65 mmol) was added to a stirred solution of 2-aminopropane-1,3-diol (0.3 g, 3.29 mmol) and 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde (0.196 g, 0.659 mmol, prepared as in G. B. Evans, R. H. Furneaux, A, Lewandowicz, V. L. Schramm and P. C. Tyler, J. Med. Chem., 2003, 46, 3412) in MeOH (5 ml). Sodium cyanoborohydride (0.062 g, 0.988 mmol) was added and the mixture was stirred at rt overnight. The solvent was evaporated and the residue chromatographed on silica gel (CH2Cl2-MeOH-28% NH4OH, 95:5:0.5 then 9:1:0.05) to give 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-propane-1,3-diol (0.188 g, 77%) as a colourless solid. 1H NMR (CD3OD) δ 8.42, (s, 1H), 7.65 (s, 1H), 7.25-7.16 (m, 5H), 5.75 (s, 2H), 4.50 (s, 2H), 4.10 (s, 3H), 4.03 (s, 2H), 3.68 (dd, J=11.2, 5.9 Hz, 2H), 3.58 (dd, J=11.2, 5.9 Hz, 2H), 2.81 (pentet, J=5.6 Hz, 1H). 13C NMR (CD3OD, 75.5 MHz, referenced to centre line of CD3OD at δ 49.0) δ 157.9, 150.8, 150.6, 138.7, 134.1, 129.3, 128.8, 128.6, 117.0, 116.2, 78.5, 71.5, 62.5 (CH2X2), 61.3, 54.3, 41.4. +ESMS Found 373.1865 (M+H)+ C19H25N4O4 requires 373.1876.

後処理

  1. custom0.196 g, 0.659 mmol, prepared as in G
  2. customThe solvent was evaporated
  3. customthe residue chromatographed on silica gel (CH2Cl2-MeOH-28% NH4OH, 95:5:0.5

出典と根拠

ORDレコード
ord-119f2aba548e49fb8f56bc40c5ba70d2
出典データセット
uspto-grants-2014_10
特許番号
US08853224B2

反応ノート

読み込み中…