Thionyl Chloride → HCID 18798244, compound

HRID 1003729Notes

Reaction equation

HRID 1003729 reaction equation
[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11]Cl)=[C:6]([CH3:13])[C:5](=[O:14])[N:4]([CH3:15])[C:3]1=[O:16].CN1C(NCCCO)=C(C)C(=O)N(C)C1=O.S(Cl)(Cl)=O.[OH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C1(C)C(C)=CC=CC=1.C(N(CCC)CCC)CC>[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][N:47]2[CH2:46][CH2:45][N:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[OH:37])[CH2:49][CH2:48]2)=[C:6]([CH3:13])[C:5](=[O:14])[N:4]([CH3:15])[C:3]1=[O:16]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 70530o-(1-Piperazinyl)phenolHCID 18798239HCID 18798239, compoundHCID 18798255HCID 18798255, compound

Product 1

HCID 18798244HCID 18798244, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 7616TripropylamineSolvent

Procedure

The 1,3,5-trimethyl-6-(3-chloropropylamino)-2,4(1H,3H)-pyrimidinedione prepared from 6.8 g (30 mmol) of 1,3,5-trimethyl-6-(3-hydroxypropylamino)-2,4(1H,3H)pyrimidinedione with thionyl chloride is refluxed for 15 h with 4.5 g (25 mmol) of 1-(2-hydroxyphenyl)piperazine in 140 ml of xylene and 20 ml of tripropylamine. The dark oil obtained after customary work-up is purified by column chromatography on silica gel using dichloromethane/methanol (1-10%). From the product fractions, the fumarate is precipitated from ethyl acetate/ethanol using fumaric acid, yield 5.9 g (47%), m.p. 203-205° C.

Workup

  1. customThe dark oil obtained after customary work-up
  2. customis purified by column chromatography on silica gel
  3. customFrom the product fractions, the fumarate is precipitated from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-ff53a2d14a544b2b875fa269376cbe39
Source dataset
uspto-grants-2000_04
Patent number
US06046329

Reaction notes

Loading…