Ethyl Acetate → 5-(benzyloxyMethyl)-4-Methoxy-5H-pyrrolo[3,2-d]pyriMidine

HRID 1429700Notes

Reaction equation

Cl[C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].Cl[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[CH2:24][O:25]C(C)=O>C1COCC1.CO>[CH2:16]([O:15][CH2:14][N:10]1[C:3]2[C:2]([O:25][CH3:24])=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.53 g, 10.0 mmol) in 30 mL of THF was added NaH (560 mg, 14.0 mmol, 60% in mineral oil) by portion under N2. After the mixture was cooled to 0° C., benzyl chloromethyl ether (1.71 mL, 13.0 mmol) was added. Then the mixture was stirred at RT for 1 h (monitored by TLC 40% EtOAc/Hex). 8 mL of anhydrous MeOH was added into the reaction mixture followed by NaH (400 mg, 10.0 mmol, 60% mineral oil) by portion. The resulting mixture was stirred at RT overnight. After being quenched with sat. NH4Cl, the mixture was extracted with EtOAc (3×). The organic layer was washed with sat. NaHCO3 (aq), brine, then dried (MgSO4) and concentrated. Silica gel chromatography (elution with 0-30% EtOAc/Hex) afforded product 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine (2.36 g).

Workup

customAfter being quenched with sat. NH4Cl
extractionthe mixture was extracted with EtOAc (3×)
washThe organic layer was washed with sat. NaHCO3 (aq), brine
dry with materialdried (MgSO4)
concentrationconcentrated
washSilica gel chromatography (elution with 0-30% EtOAc/Hex)

Sources & evidence

ORD record: ord-f37f3904fb4644708a59548fcf2ffab9
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940748B2

Reaction notes

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