Methanol → HCID 86699683, compound

HRID 1487187Notes

Reaction equation

HRID 1487187 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:23])[C:5]2[C:10]3([CH2:12][CH2:11]3)[C:9](=O)[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:7]=1.CO>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([Cl:23])[C:5]2[C:10]3([CH2:12][CH2:11]3)[CH2:9][N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86699682HCID 86699682, compound

Product 1

HCID 86699683HCID 86699683, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2′,4′-dichloro-7′-(4-methoxybenzyl)spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′H)-one (14.0 g, 40.0 mmol) in tetrahydrofuran (200 mL) was added 94% Borane-methyl sulfide complex (8.2 mL, 80.0 mmol) dropwise under nitrogen atmosphere. After the addition was over, the reaction mixture was heated to 60° C. overnight. When the reaction was completed, methanol was added to the reaction solution at 0° C., concentrated in vacuum and the residue was purified by silica gel chromatography to afford the product as a white solid (8.4 g, yield 62.4%). 1H NMR (400 MHz, CDCl3) δ ppm 7.20 (d, J=8.6 Hz, 2H), 6.91-6.86 (m, 2H), 4.59 (s, 2H), 3.81 (s, 3H), 3.48 (s, 2H), 1.71 (q, J=4.9 Hz, 2H), 0.82 (q, J=4.9 Hz, 2H).

Workup

  1. additionAfter the addition
  2. concentrationconcentrated in vacuum
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-482622e5902d4bbb92c82cf76360732a
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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