Propylene Glycol → HCID 18315690, compound

HRID 275929Notes

Reaction equation

HRID 275929 reaction equation
[CH3:1][C:2]1[C:3]([Cl:16])=[N:4][C:5]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[N:6][C:7]=1[CH3:8].[CH2:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][NH:18]1.C(N([CH2:32][CH3:33])CC)C.[CH2:34](O)[CH:35](O)[CH3:36]>ClCCl>[ClH:16].[CH3:1][C:2]1[C:3]([N:18]2[CH2:19][CH2:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17]2)=[N:4][C:5]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:33]=[CH:32][CH:36]=[CH:35][CH:34]=3)[N:14]=2)=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 183156854-Chloro-5,6-dimethyl-N-(4-methyl-2-thiazolyl)-2-pyrimidinamine

Product 1

HCID 18315690HCID 18315690, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture solution of 5,6-dimethyl-2-(4-methylthiazol-2-yl)amino-4-chloropyrimidine (0.36 g, 1.14 mmol), 1,2,3,4-tetrahydroisoquinoline(0.16 ml, 1.25 mmol), triethylamine(0.16 ml, 1.25 mmol) and propyleneglycol(1.1 ml) was heated to 140° C., stirred for 5 hours, diluted with dichloromethane, and then washed with water. The separated organic layer was dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified by a silica gel column chromatography using, a soluton of ethyl acetate and hexane (1:3) as a eluent. After evaporating of the solvent, the residual oil was dissolved in a solution of ethyl ether and ethyl acetate and treated with ethylether saturated with hydrochloric acid. The resulting solid was filtered and dried to give 0.18 g of the titled compound.

Workup

  1. washwashed with water
  2. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe resulting residue was purified by a silica gel column chromatography
  5. customAfter evaporating of the solvent
  6. dissolutionthe residual oil was dissolved in a solution of ethyl ether and ethyl acetate
  7. additiontreated with ethylether saturated with hydrochloric acid
  8. filtrationThe resulting solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-61b403ab3cea4ce892220435c127f985
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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