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

HRID 533201노트

반응식

HRID 533201 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-119f2aba548e49fb8f56bc40c5ba70d2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853224B2

반응 노트

불러오는 중…