Methanol → HCID 11630104, compound

HRID 1175728Notes

Reaction equation

HRID 1175728 reaction equation
[N:1]1([C:7]2[C:8]3[N:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO>C(Cl)Cl.[O-2].[Mn+2].O=[Mn]=O>[N:1]1([C:7]2[C:8]3[N:16]=[C:15]([CH:17]=[O:18])[CH:14]=[CH:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 887MethanolHCID 66927704HCID 66927704, compound2×

Product 1

HCID 11630104HCID 11630104, compound

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[4-(1-piperidinyl)pyrido[3,2-d]pyrimidin-6-yl]methanol (Intermediate 1.6) (3.95 g; 16.2 mmol; 1.00 eq.) was dissolved in DCM (160 mL). The solution was cooled down to 0° C. and manganese oxide (16.5 g; 0.162 mol; 10 eq.) was added. The reaction was stirred 5 min at 0° C. then overnight at rt. To complete the conversion, MnO2 was added after 12 hours and 20 hours (two batches of 4.96 g; 48.48 mmol; 3 eq.). After 20 hours, the reaction was complete. MeOH (100 mL) was added and the mixture was filtered through Celite, and widely rinsed with DCM/MeOH 1:1 mixture. Solvents were removed under reduced pressure to give 4-(1-piperidinyl)pyrido[3,2-d]pyrimidine-6-carbaldehyde (Intermediate 1.7). This product was used in the next step without further purification. Amount: 4.1 g; Formula: C13H14ON4; HPLC Purity: 58.84%; LC-MS: M/Z ESI: Rt (min) 1.53; 243.06 (M+1); HPLC (H2O TFA 0.1%-ACN TFA 0.05%): Rt (min); Area %=1.39; 58.84. 1H NMR (DMSO-d6) δ 9.95 (s, 1H), 8.52 (s, 1H), 8.16 (m, 2H), 4.46 (1, 4H), 1.70 (1, 6H).

Workup

  1. customovernight
  2. customat rt
  3. additionwas added after 12 hours and 20 hours (two batches of 4.96 g; 48.48 mmol; 3 eq.)
  4. waitAfter 20 hours
  5. filtrationthe mixture was filtered through Celite
  6. washwidely rinsed with DCM/MeOH 1:1 mixture
  7. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-29b73fbd08e5424985dad1c16a6b22d8
Source dataset
uspto-grants-2010_11
Patent number
US07842698B2

Reaction notes

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