Diethyl Ether → 2-[[2-Hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-5-[(6-methyl-3-pyridinyl)methyl]-4-(3H)-pyrimidinone

HRID 1589542Notes

Reaction equation

HRID 1589542 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:17])[NH:11][C:12](SC)=[N:13][CH:14]=2)=[CH:4][CH:3]=1.[NH2:18][CH2:19][CH:20]([OH:36])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:24]=1.C(OCC)C>C(Cl)(Cl)Cl>[OH:36][CH:20]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:24]=1)[CH2:19][NH:18][C:12]1[NH:11][C:10](=[O:17])[C:9]([CH2:8][C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 127838275-[(6-Methylpyridin-3-yl)methyl]-2-(methylsulfanyl)pyrimidin-4(3H)-oneHCID 131898251-Amino-3-{3-[(piperidin-1-yl)methyl]phenoxy}propan-2-ol2×

Product 1

HCID 202460252-[[2-Hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-5-[(6-methyl-3-pyridinyl)methyl]-4-(3H)-pyrimidinoneYield 38.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5-(6-methyl-3-pyridinylmethyl)-2-methylthio-4(3H)-pyrimidinone (1.24 g) and 1-amino-3-[3-[1-piperidinylmethyl]phenoxy]-2-propanol (Compound A) (1.32 g) was heated at 120° for 1.5 h and then at 130°-140° for 2.5 h. The resulting brown glass was dissolved in chloroform (25 ml) and added to stirred dry diethyl ether (250 ml) to precipitate a white solid (1.5 g). This solid was recrystallised from ethyl acetate to give the title compound (0.9 g) as a white solid, m.p. 115°-117°.

Workup

  1. temperaturewas heated at 120° for 1.5 h
  2. additionadded
  3. customto precipitate a white solid (1.5 g)
  4. customThis solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2cb68b6d2ead44acb0f012cf5fdd7434
Source dataset
uspto-grants-1986_02
Patent number
US04571394

Reaction notes

Loading…