Water → N-allyl-2-chloro-8-(4-fluorophenyl)-N,6-dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

HRID 474277Notes

Reaction equation

HRID 474277 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][N:10]([CH3:12])[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:6]=2[N:7]=1.[CH3:21][NH:22][CH2:23][CH:24]=[CH2:25].O>CN1C(=O)CCC1>[CH2:23]([N:22]([CH3:21])[C:4]1[C:5]2[CH2:11][N:10]([CH3:12])[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 962WaterHCID 69391N-MethylallylamineHCID 580753632,4-Dichloro-8-(4-fluorophenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-D]pyrimidine

Product 1

HCID 86668120N-allyl-2-chloro-8-(4-fluorophenyl)-N,6-dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amineYield 100%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture of 2,4-dichloro-8-(4-fluorophenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (Preparation V, 408 mg, 1.307 mmol) in NMP (13 mL) was added N-methylprop-2-en-1-amine (465 mg, 6.53 mmol). The resulting reaction mixture was stirred at rt overnight. Water (50 mL) was added to the mixture and stirred for 30 min. The mixture was filtered to get a light tan solid which was dried and purified by flash column chromatography eluting with 30 to 100% EtOAc/Hexane to get N-allyl-2-chloro-8-(4-fluorophenyl)-N,6-dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (453 mg, 100% yield). LC-MS (M+H)+=347.1.

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 30 min
  3. filtrationThe mixture was filtered
  4. customto get a light tan solid which
  5. customwas dried
  6. custompurified by flash column chromatography
  7. washeluting with 30 to 100% EtOAc/Hexane

Sources & evidence

ORD record
ord-2c4a11379c1b49f49a229c1e0a892e6d
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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