Benzylamine → HCID 5328256, compound

HRID 1059623Notes

Reaction equation

HRID 1059623 reaction equation
CS[C:3]1[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([NH:20][C:3]1[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 232404654-Methylthiopyrido[3,4-d]pyrimidine

Product 1

HCID 5328256HCID 5328256, compoundYield 20%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-methylthiopyrido[3,4-d]pyrimidine (74 mg, 0.41 mmol)(see a previous experimental), and benzylamine (1 mL) is heated to 100° C. for 2 h. On cooling the mixture is concentrated under reduced pressure and purified directly by preparative tlc on silica gel eluting with CH2Cl2, to yield 4-(benzylamino)pyrido[3,4-d]pyrimidine (21.2 mg, 20%). 1H NMR (DMSO) δ 9.21 (1H, t, J=5.8 Hz), 9.19 (1H, s), 8.63 (1H, d, J=5.8 Hz), 8.58 (1H, s), 8.20 (1H, d, J=5.1 Hz), 7.41-7.30 (4H, m), 7.26 (1H, t, J=7.1 Hz).

Workup

  1. temperatureOn cooling the mixture
  2. concentrationis concentrated under reduced pressure
  3. custompurified directly by preparative tlc on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-dde9aad580e249c49675d47375470342
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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