Pyridine → US9296747, Example 2

HRID 930500Notes

Reaction equation

HRID 930500 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[CH2:23][NH:22][CH2:21][CH2:20][C:18]=3[N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:24]([O:32]C(=O)C1C=CC=CC=1)(=O)[C:25]1[CH:30]=[CH:29][CH:28]=C[CH:26]=1.[N:41]1C=CC=CC=1>C(Cl)Cl>[N:41]1[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([N:22]2[CH2:21][CH2:20][C:18]3[N:19]=[C:14]([NH:13][C:5]4[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:15]=[CH:16][C:17]=3[CH2:23]2)=[O:32])[CH:26]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7167Benzoic anhydrideHCID 118970894N-(3,4,5-Trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 118970905US9296747, Example 2

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(3,4,5-Trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (75 mg, 0.24 mmol) in CH2Cl2 (1.5 mL) was cooled to 0° C. and treated with benzoic anhydride (56.7 mg, 0.251 mmol) and pyridine (22 microliter, 0.273 mmol). After 1 hour the reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was collected, dried and concentrated. The residue was purified by silica gel chromatography (15-40% acetone/CH2Cl2). The product containing fractions were concentrated to give the title compound (75 mg).

Workup

  1. washwashed with water
  2. customThe organic phase was collected
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (15-40% acetone/CH2Cl2)
  6. additionThe product containing fractions
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-7b5cbb867ce644b0b9ac7ca2063ba75d
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

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