Triethylamine → HCID 22736800, compound

HRID 50801Notes

Reaction equation

HRID 50801 reaction equation
F[C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH2:20]([N:22](CC)CC)C.Cl.[CH3:28]N>C(O)(C)C>[Br:19][C:15]1[CH:14]=[C:13]([N:12]([C:8]2[C:9]3[CH:10]=[N:11][C:2]([NH:22][CH3:20])=[CH:3][C:4]=3[N:5]=[CH:6][N:7]=2)[CH3:28])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5328251N-(3-bromophenyl)-7-fluoropyrido[4,3-d]pyrimidin-4-amineHCID 6364545Methylamine hydrochloride

Product 1

HCID 22736800HCID 22736800, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-fluoro-4-(3-bromoanilino)-pyrido[4,3-d]pyrimidine (100 mg, 0.31 mmole), triethylamine (4.4 mL, 32 mmole) and methylamine hydrochloride (2.12 g, 32 mmole) in isopropanol (30 mL) contained in a steel bomb is stirred at 100° C. (oil bath) for 5 h. The resulting mixture is concentrated under vacuum, basified with aqueous Na2CO3, diluted with water and extracted with EtOAc (3×100 mL). Chromatography of this extract on silica gel (1-2% MeOH/CH2Cl2) gives 4-[N-(3-bromophenyl)-N-methylamino]-7-methylaminopyrido[4,3-d]pyrimidine (23 mg, 21%) as a pale yellow solid. 1H NMR (DMSO) δ 8.14 (1H, s), 7.79 (1H, s), 7.30 (1H, t, J=8.0 Hz), 7.20 (1H, ddd, J=7.9, 1.8, 0.8 Hz), 7.03 (1H, brq, J=4.9 Hz), 7.01 (1H, t, J=1.9 Hz), 6.82 (1H, ddd, J=7.8, 1.8, 0.9 Hz), 6.25 (1H, s), 3.40 (3H, s), 2.73 (3H, d, J=4.9 Hz).

Workup

  1. concentrationThe resulting mixture is concentrated under vacuum
  2. additiondiluted with water
  3. extractionextracted with EtOAc (3×100 mL)
  4. extractionChromatography of this extract on silica gel (1-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bc3d17e2a88c4d1b97873af3faf088ef
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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