تفاعل #92181

معادلة التفاعل

6-bromo-5-(bromomethyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde

Compound 2

6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde

2-iodoxybenzoic acid

→

ethyl 6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydro thieno[2,3-d]pyrimidine-5-carbaldehyde

المردود 57.5%

المذيبات

DMSO

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to RT
2. 2
   استخلاصextracted with EA (3×10 mL)
3. 3
   غسيلThe combined organic layers were washed with aq. NH4Cl (20 mL)
4. 4
   تجفيفdried over Na2SO4
5. 5
   تركيزconcentrated to a residue which
6. 6
   أخرىwas purified by chromatography
7. 7
   غسيلeluted with PE/EA (5:1 to 1:1)

الإجراء التجريبي

To a solution of 6-bromo-5-(bromomethyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 2, Step 3, 800 mg, 1.61 mmol) in DMSO (10 mL) was added 2-iodoxybenzoic acid (541.7 mg, 1.93 mmol). The reaction was heated at 50° C. for 1.5 h, cooled to RT, diluted with water (20 mL) and extracted with EA (3×10 mL). The combined organic layers were washed with aq. NH4Cl (20 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1 to 1:1) to give ethyl 6-bromo-1-methyl-2,4-dioxo-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-1,2,3,4-tetrahydro thieno[2,3-d]pyrimidine-5-carbaldehyde (400 mg, 57.5% yield) as a white solid. LCMS: [MH+-THP] 347 and TR=1.665 min.

المصدر