5-Hydroxyindole → tert-butyl 4-(1H-indol-5-yloxy)-5-methyl-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 45094Notes

Reaction equation

HRID 45094 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:16]([CH3:17])[C:15]2[C:14](=[O:18])[NH:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:52]1[CH2:62][CH2:61][N:60]2[C:55](=NC[CH2:58][CH2:59]2)[CH2:54][CH2:53]1.OC1C=C2C(=CC=1)NC=C2>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH:16]([CH3:17])[C:15]2[C:14]([O:18][C:62]3[CH:52]=[C:53]4[C:59](=[CH:58][CH:61]=3)[NH:60][CH:55]=[CH:54]4)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 160545-HydroxyindoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724699PyBOPHCID 1361587835-Methyl-4-oxo-3,4,5,7-tetrahydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Product 1

HCID 59394355tert-butyl 4-(1H-indol-5-yloxy)-5-methyl-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. waitThe reaction is left
  2. customThe reaction mixture is then evaporated
  3. additionthe crude product is added to a silica gel column
  4. washis eluted with heptane/ethyl acetate (100:0 to 60:40)

Sources & evidence

ORD record
ord-fe4e12d38a9149a69e421085974ae94b
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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