Reaction #62731

Reaction equation

2,4-diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidine

→

title compound

Yield 37.0%

2,4-Diamino-5-(7,8-dimethoxy-2-methyl-2H-1-benzopyran-5-ylmethyl)pyrimidin

Yield 37.0%

Solvents

N,N-diethylaniline

Conditions

Workup

1. 1
   FiltrationThe hot solution was filtered
2. 2
   Otherto remove dark tarry material
3. 3
   TemperatureThe filtrate was cooled
4. 4
   workup.ADDITIONdiluted with hexanes (200 mL)
5. 5
   OtherThe precipitate (3.8 g) was recrystallized from ethanol

Procedure

A solution of 2,4-diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidine (4.28 g, 13.0 mmol) in N,N-diethylaniline (200 mL) was refluxed under nitrogen for 0.5 hr. The hot solution was filtered to remove dark tarry material. The filtrate was cooled and diluted with hexanes (200 mL). The precipitate (3.8 g) was recrystallized from ethanol to give title compound as off-white powder (1.56 g, 37%); mp 219°-221° dec. Anal. Calcd for C17H20N4O3 : C, 62.18; H, 6.14; N, 17.06. Found: C, 61.91; H, 6.20; N, 16.93.

Source