1-Butanol → {4-[(2-Amino-6-chloropyrimidin-4-yl)amino]cyclopent-2-en-1-yl}methanol

HRID 1861664Notes

Reaction equation

HRID 1861664 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.C([N:12]([CH2:15][CH3:16])CC)C.[CH2:17]([OH:21])[CH2:18][CH2:19][CH3:20]>>[NH2:1][C:2]1[N:3]=[C:4]([NH:12][CH:15]2[CH2:16][CH:18]([CH2:17][OH:21])[CH:19]=[CH:20]2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 14503066{4-[(2-Amino-6-chloropyrimidin-4-yl)amino]cyclopent-2-en-1-yl}methanol

Procedure

To 14 mmol of crude 2a, 2-amino-4,6-dichloropyrimidine (3.74 g, 22.8 mmol), triethylamine (15 ml) and n-butanol (75 ml) were added and the mixture was refluxed for 48 hr. The volatile solvents were removed, residue was treated with methanol to separate the undissolved byproduct (the double pyrimidine nucleoside). The methanol solution was absorbed on silica gel (8 g) packed into a column (4.0×14 cm) and eluted with CHCl-MeOH (40:1) to yield 1.52 g (42%) of crude 4a. The product was recrystalized from ethyl acetate to yield 4a; mp 132-134° C., MS (30 ev, 200° C.); m/e 240 and 242 (M+ and M++2), 209 (M+−31), 144 (B+); IR: 3600-3000 (NH2, OH), 1620,1580 (C═C, C═N); Anal. (C10H13ClN4O) C,H,N.

Workup

  1. temperaturethe mixture was refluxed for 48 hr
  2. customThe volatile solvents were removed
  3. additionresidue was treated with methanol
  4. customto separate the undissolved byproduct (the double pyrimidine nucleoside)
  5. customThe methanol solution was absorbed on silica gel (8 g)
  6. washeluted with CHCl-MeOH (40:1)

Sources & evidence

ORD record
ord-bff2446fea0a4ad59b15246aabe51420
Source dataset
uspto-grants-2003_03
Patent number
US06534512B1

Reaction notes

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