4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → HCID 69794413, compound

HRID 397435Notes

Reaction equation

HRID 397435 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].[CH2:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]([C:30]2[NH:34][C:33]([CH:35]=O)=[C:32]([CH3:37])[CH:31]=2)=[O:29])[CH2:24][CH2:23]1)[CH3:21]>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:35][C:33]4[NH:34][C:30]([C:28]([N:25]5[CH2:24][CH2:23][N:22]([CH2:20][CH3:21])[CH2:27][CH2:26]5)=[O:29])=[CH:31][C:32]=4[CH3:37])[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 22390968HCID 22390968, compound

Product 1

HCID 69794413HCID 69794413, compoundYield 73%

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-(4-ethyl-piperazine-1-carbonyl)-3-methyl-1H-pyrrole-2-carbaldehyde (74.8 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for overnight. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 93 mg (73%) of the title compound. 1H NMR (300 MHz, DMSN d6) δ 3.40 (br s, 1H, NH), 11.81 (br s, 1H, NH), 9.28 (br s, 1H), 8.33 (s, 1H), 7.72 (m, 1H), 7.33-7.45 (m, 3H), 6.58 (m, 1H), 3.68 (m, 4H, 2×CH2), 2.31-2.42 (m, 6H), 2.22 (s, 3H, CH3), 1.01 (t, J=7.2 Hz, 3H, CH2CH3). MS 510 [M++1].

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-7257670bc5f9417c8e838e25d9b3b374
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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