Triphenylphosphine → 2-Chloro-4-(N-(2-cyclohexylethyl)anilino)pyrimidine

HRID 347753Notes

Reaction equation

HRID 347753 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:34]1([CH2:40][CH2:41]O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:41][CH2:40][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 205082-Cyclohexylethanol2×HCID 5462977Diethyl azodicarboxylate2×HCID 219953492-Chloro-N-phenylpyrimidin-4-amine

Product 1

HCID 210837392-Chloro-4-(N-(2-cyclohexylethyl)anilino)pyrimidineYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-anilinopyrimidine (Reference Example A-9, 700 mg, 3.4 mmol) was dissolved in DCM (70 ml), triphenyl phosphine (1.07 g, 4.1 mmol) and 2-cyclohexyl ethanol (0.57 ml, 4.1 mmol) were added followed by dropwise addition of DEAD (0.646 ml, 4.1 mmol). After 1 hour additional triphenyl phosphine (0.5 g, 2 mmol), 2-cyclohexyl ethanol (0.28 ml, 2 mmol) and DEAD (0.320 ml, 2 mmol) were added and the reaction mixture was stirred overnight at ambient temperature. The solvent was evaporated off and the residue was purified by flash chromatography using EtOAc/petroleum ether (15/85, then 20/80) as the eluent. The solvent was evaporated to give the title product as a colourless oil (368 mg, 37%). NMR (400 MHz, 353K): 0.90 (m, 2H), 1.20 (m, 3H), 1.30 (m, 1H), 1.65 (m, 7H), 3.90 (t, 2H), 4.05 (m, 1H), 6.10 (d, 1H), 7.34 (d, 2H), 7.43 (t, 1H), 7.54 (t, 2H), 7.95 (d, 1H); m/z (ES+) 316 and 318 (MH+).

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was purified by flash chromatography
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-427526bfef9445d2a4b22b033018965a
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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