Reaction #505013

Reaction equation

2,4-diamino-6-hydroxypyrimidine

chloroacetaldehyde

sodium acetate

DMF

→

title compound

Yield 52.3%

2-Amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

Yield 52.3%

Solvents

water

Conditions

Workup

1. 1
   FiltrationThe resulting solid was collected by filtration
2. 2
   Washwashed with water (50 mL×3)
3. 3
   ConcentrationThe mother liquor was concentrated
4. 4
   Otherto give additional material which
5. 5
   Washwas washed with water (50 mL×3)
6. 6
   OtherThe combined solid materials were recrystallized from MeOH

Procedure

A mixture of 2,4-diamino-6-hydroxypyrimidine (300 g, 2.37 mol), chloroacetaldehyde (50% aq. solution, 382 g, 2.43 mol, 303 mL, 1.02 eq.), sodium acetate (195 g, 2.37 mol), DMF (2.5 L), and water (360 mL) was stirred mechanically at rt for 2 days. The resulting solid was collected by filtration, and washed with water (50 mL×3). The mother liquor was concentrated to give additional material which was washed with water (50 mL×3). The combined solid materials were recrystallized from MeOH to give the title compound as a white powder (186 g, 52% yield, HPLC purity: 100%). tR: 2.21 min. 1H-NMR (DMSO-d6) δ 11.00 (br. s, 1H), 10.33 (br. s, 1H), 6.63 (q, 1H), 6.21 (q, 1H), 6.12 (br. s, 2H).

Source