반응 #73372

ord-fe4e12d38a9149a69e421085974ae94b

반응 방정식

Oc1ccc2[nH]ccc2c1
5-hydroxyindole
C1CCC2=NCCCN2CC1
DBU
CC1c2c(nc[nH]c2=O)CN1C(=O)OC(C)(C)C
5-methyl-4-oxo-3,4,5,7-tetrahydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester
F[P-](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1
PyBOP
CC1c2c(ncnc2Oc2ccc3[nH]ccc3c2)CN1C(=O)OC(C)(C)C
title compound
CC1c2c(ncnc2Oc2ccc3[nH]ccc3c2)CN1C(=O)OC(C)(C)C
(±)-4-(1H-Indol-5-yloxy)-5-methyl-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.WAITThe reaction is left
  2. 2
    기타The reaction mixture is then evaporated
  3. 3
    workup.ADDITIONthe crude product is added to a silica gel column
  4. 4
    세척is eluted with heptane/ethyl acetate (100:0 to 60:40)

실험 절차

To a solution of 5-methyl-4-oxo-3,4,5,7-tetrahydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1 g, 3.98 mmol) in acetonitrile (40 ml), PyBOP (2.69 g, 5.17 mmol) is added, followed by DBU (1.200 ml, 7.96 mmol). After 20 min, 5-hydroxyindole (1.060 g, 7.96 mmol) is added. The reaction is left stirring at rt overnight. The reaction mixture is then evaporated, the crude product is added to a silica gel column and is eluted with heptane/ethyl acetate (100:0 to 60:40) to give the title compound. MS (ESI) m/z 367.05 (M+1).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08541432B2uspto-grants-2013_09