Reaction #809429

Reaction equation

2,4-diamino-6-hydroxypyrimidine

AcONa

3-bromo-4-methyl-pentanal

→

2-amino-5-isopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

Yield 40.0%

Solvents

CH3CN

H2O

Conditions

Workup

1. 1
   workup.DISSOLUTIONgradually dissolved
2. 2
   Otherthe desired pyrrolo[2,3-d]pyrimidine precipitated
3. 3
   FiltrationThe precipitate was collected by filtration
4. 4
   Washwashed with MeOH

Procedure

A suspension of 2,4-diamino-6-hydroxypyrimidine (6.68 g, 50 mmol), AcONa (8.3 g 100 mmol) and 3-bromo-4-methyl-pentanal (8.76 g, 50 mmol) in CH3CN (100 mL) and H2O (100 mL) was stirred at 25° C. overnight whereupon the starting materials gradually dissolved and the desired pyrrolo[2,3-d]pyrimidine precipitated. The precipitate was collected by filtration and washed with MeOH to give 2-amino-5-isopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (3.80 g, 40%). HPLC Rt: 4.408 min. 1H-NMR (DMSO-d6): δ 10.58 (s, 1H), 10.10 (s, 1H), 6.30 (s, 1H), 5.97 (s, 2H), 3.03 (7, 1H), 1.20 (s, 3H), 1.19 (s, 3H).

Source