2,4-Diamino-5-pyrimidinemethanol → HCID 23323056, compound

HRID 279972

Reaction equation

HRID 279972 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH2:10][CH2:9][CH2:8]2.[NH2:13][C:14]1[N:19]=[C:18]([NH2:20])[C:17]([CH2:21]O)=[CH:16][N:15]=1>>[NH2:13][C:14]1[N:19]=[C:18]([NH2:20])[C:17]([CH2:21][C:5]2[CH:6]=[C:7]3[C:12](=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:11][CH2:10][CH2:9][CH2:8]3)=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 2958782,4-Diamino-5-pyrimidinemethanolHCID 52003458-Methoxy-1,2,3,4-tetrahydroquinoline

Product 1

HCID 23323056HCID 23323056, compound

Procedure

8-Methoxy-1,2,3,4-tetrahydroquinoline (J. L. Neumeyer and J. G. Cannon, J. Pharm. Sci., 51, 804 (1962)) (2.88 g) was treated by the method of Example 1 with 2,4-diamino-5-hydroxymethylpyrimidine. The product crystallized from the reaction mixture as an off-white solid, which was washed with water and treated with ammonia, followed by recrystallization from absolute ethanol (5.0 g). A slight impurity was removed on a silica gel column, which was eluted with 19:1 methylene chloride:methanol, taken to dryness, and recrystallized once more from absolute ethanol; m.p., 201°-203° C. Anal. Calcd. for C15H19N5O: C, 63.14; H, 6.71; N, 24.54. Found: C, 63.23; H, 6.75; N, 24.47.

Workup

  1. customThe product crystallized from the reaction mixture as an off-white solid, which
  2. washwas washed with water
  3. additiontreated with ammonia
  4. customfollowed by recrystallization from absolute ethanol (5.0 g)
  5. customA slight impurity was removed on a silica gel column, which
  6. washwas eluted with 19:1 methylene chloride
  7. customrecrystallized once more from absolute ethanol
  8. custom201°-203° C

Sources & evidence

ORD record
ord-50836c5c003c49089c0b13dcfbca704d
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Linked notes

Loading…