2-Fluorophenyl isocyanate → 1-[4-(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-6-methyl-pyridin-2-yl]-3-(2-fluoro-phenyl)-urea

HRID 736345Notes

Reaction equation

HRID 736345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[NH2:11][C:12]1[C:13]2[C:20]([C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH2:30])[CH:24]=3)=[O:22])=[CH:19][N:18]([CH:31]([CH3:33])[CH3:32])[C:14]=2[N:15]=[CH:16][N:17]=1>N1C=CC=CC=1>[NH2:11][C:12]1[C:13]2[C:20]([C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH:30][C:9]([NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[O:10])[CH:24]=3)=[O:22])=[CH:19][N:18]([CH:31]([CH3:33])[CH3:32])[C:14]=2[N:15]=[CH:16][N:17]=1

Participants

4

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 68902711(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methyl-pyridin-4-yl)-methanone

Product 1

HCID 689034621-[4-(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-6-methyl-pyridin-2-yl]-3-(2-fluoro-phenyl)-ureaYield 72.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Fluoro-2-isocyanato-benzene (48.5 mg, 035 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methyl-pyridin-4-yl)-methanone (100 mg, 0.32 mmol) in pyridine (2 mL). The mixture was stirred for 2 h at room temperature. The reaction mixture was quenched with H2O (2 mL) and concentrated in vacuo. The resulting residue was triturated with MeOH, filtered, and dried to afford the title compound as an off-white solid (104 mg, 72%). MS: 448.3 (MH+); HPLC Rf: 6.36 min. (HPLC method 4).

Workup

  1. customThe reaction mixture was quenched with H2O (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was triturated with MeOH
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-87ba31e7e40c407283a609268eed9d7f
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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