6-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one → HCID 16657115, compound

HRID 1176193Notes

Reaction equation

HRID 1176193 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.C([NH:32][CH2:33][CH:34]1[O:38][C:37]2[CH:39]=[CH:40][C:41]([NH2:43])=[CH:42][C:36]=2[O:35]1)(OC(C)(C)C)=O>C(O)(=O)C>[NH2:32][CH2:33][CH:34]1[O:38][C:37]2[CH:39]=[CH:40][C:41]([NH:43][C:14]3[N:15]=[CH:16][C:11]4[CH:10]=[C:9]([C:3]5[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=5[Cl:8])[C:22](=[O:23])[N:21]([CH3:24])[C:12]=4[N:13]=3)=[CH:42][C:36]=2[O:35]1

Participants

4

Reactant 2

HCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 131728550HCID 131728550, compound

Product 1

HCID 16657115HCID 16657115, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.384 g of compound of formula (II), 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, and 0.266 g of compound of formula (III), (R/S)-2-(N-Boc-aminomethyl)-1,3-benzodioxol-5-ylamine, is heated in 4 ml of acetic acid at 80° C. for 2 h. The reaction medium is subsequently concentrated by half under vacuum, then taken up in water and ethyl acetate and brought to pH 6 with a saturated NaHCO3 solution; the organic phase is separated by settling, washed with water and then a saturated NaCl solution, dried over sodium sulfate and evaporated. The crude product obtained is purified by flash chromatography on silica with a gradient of 0 to 1% of methanol in dichloromethane. 0.252 g of expected product is obtained in the form of a yellow powder.

Workup

  1. concentrationThe reaction medium is subsequently concentrated by half under vacuum
  2. customthe organic phase is separated
  3. washwashed with water
  4. dry with materiala saturated NaCl solution, dried over sodium sulfate
  5. customevaporated
  6. customThe crude product obtained
  7. customis purified by flash chromatography on silica with a gradient of 0 to 1% of methanol in dichloromethane

Sources & evidence

ORD record
ord-d6912713bd754ab8a64821c08b4759bd
Source dataset
uspto-grants-2010_11
Patent number
US07842806B2

Reaction notes

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