Diisopropylethylamine → 2-(4-Ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-4-ylamino]ethyl}-acetamide

HRID 2121617Notes

Reaction equation

HRID 2121617 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:8]=[C:7]([CH3:21])[N:6]=1.[CH2:22]([O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]N)=[CH:27][C:26]=1[O:34][CH3:35])[CH3:23].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1([O:61][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH2:22]([O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][C:30]([NH:1][CH2:2][CH2:3][NH:4][C:5]2[CH:10]=[C:9]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[N:8]=[C:7]([CH3:21])[N:6]=2)=[O:61])=[CH:27][C:26]=1[O:34][CH3:35])[CH3:23]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1420764-Ethoxy-3-methoxyphenethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22034099(2-Aminoethyl){2-methyl-6-[(2,4,6-trimethylphenyl)amino]pyrimidin-4-yl}amine

Product 1

HCID 220341212-(4-Ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-4-ylamino]ethyl}-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2-aminoethyl){2-methyl-6-[(2,4,6-trimethylphenyl)amino]pyrimidin-4-yl}amine (0.36 g, 1.26 mmol), 4-ethoxy-3-methoxyphenethylamine (0.26 g, 1.26 mmol)) and N,N diisopropylethyl amine (0.24 ml, 1.38 mmol in CH2Cl2 (5 mL), add benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.61 g, 1.38 mmol) and stir at ambient temperature for 14 h. Dilute the resulting mixture with CH2Cl2 (20 mL), and wash with water (20 mL) and saturated aq NaCl (20 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify by preparative TLC (7% methanol-CH2Cl2) to obtain the title compound.

Workup

  1. washwash with water (20 mL) and saturated aq NaCl (20 mL)
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by preparative TLC (7% methanol-CH2Cl2)

Sources & evidence

ORD record
ord-21cf54611d994cfa8eea4baaafbc8e4f
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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