Toluene → HCID 22640007, compound

HRID 2415099Notes

Reaction equation

HRID 2415099 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.CC(C)([O-])C.[K+].[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][C:26]=1[O:33][CH:34]([F:36])[F:35])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>C(O)(C)(C)C>[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:1][C:2]2[C:7]([Cl:8])=[C:6]([CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=2)=[CH:27][C:26]=1[O:33][CH:34]([F:35])[F:36])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5938434-Amino-5-chloro-2,6-dimethylpyrimidineHCID 22640012HCID 22640012, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22640007HCID 22640007, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In analogy to the method described in example A5, 3.8 g (22.7 mmol) of 4-amino-5-chloro-2,6-dimethylpyrimidine, 2.8 g (25 mmol) of potassium tert-butoxide and 6.8 g (22.7 mmol) of 4-benzyloxy-3-(1,1-difluoromethoxy)benzyl chloride are reacted in 15 ml of tert-butanol and 15 ml of toluene and the product is worked up. After chromatography on silica gel (mobile phase: toluene/dioxane=5:1), the title compound is obtained as a viscous, colorless oil. 1H NMR spectrum (CDCl3, δ ppm): 7.5-7.3 (m, 5H), 7.19 (m, 1H), 7.12 (dd, 1H), 6.58 (t, 1H, J=80 Hz), 5.58 (tb, NH), 5.13 (s, 2H), 4.63 (d, 2H), 2.51 (s, 3H), 2.43 (s, 3H)

Sources & evidence

ORD record
ord-c510766b3143419daac453e5a96d88d3
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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