4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → 5-[4-(3-Chloro-4-fluoro-phenylamino)-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid

HRID 397427Notes

Reaction equation

HRID 397427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH2:18][C:17](=[O:19])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:20]([C:22]1[NH:26][C:25]([C:27]([OH:29])=[O:28])=[CH:24][C:23]=1[CH3:30])=O>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:20][C:22]4[NH:26][C:25]([C:27]([OH:29])=[O:28])=[CH:24][C:23]=4[CH3:30])[C:17](=[O:19])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 98787694-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneHCID 98988845-formyl-4-methyl-1H-pyrrole-2-carboxylic Acid

Product 1

HCID 697083575-[4-(3-Chloro-4-fluoro-phenylamino)-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (70 mg, 0.25 mmol), 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (45.9 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for 4 days.The precipitate was collected by vacuum filtration, washed with ethanol and dried, then washed with 1N HCl (3×), water (5×) and dried to give 88.8 mg (86%) of the title compound. 1H NMR (360 MHz, DMSO-d6) δ 13.55 (br s, 1H, NH), 11.84 (br s, 1H, NH), 9.28 (s, 1H), 8.34 (s, 1H), 7.74 (m, 1H), 7.43 (m, 1H), 7.41 (s, 1H), 7.38 (t, J=9.1 Hz, 1H), 6.74 (d, J=2.15 Hz, 1H), 2.22 (s, 3H, CH3). MS 414 [M++1].

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried
  4. washwashed with 1N HCl (3×), water (5×)
  5. customdried

Sources & evidence

ORD record
ord-8ed106a2f7984c79a2867445acc7bb4b
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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