4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → HCID 69794691, compound

HRID 397403Notes

Reaction equation

HRID 397403 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].[CH3:20][C:21]1[C:25]([CH2:26][CH2:27][C:28](=[O:34])[N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:24]([CH3:35])[NH:23][C:22]=1[CH:36]=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:36][C:22]4[NH:23][C:24]([CH3:35])=[C:25]([CH2:26][CH2:27][C:28](=[O:34])[N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[C:21]=4[CH3:20])[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 12095878HCID 12095878, compound

Product 1

HCID 69794691HCID 69794691, compoundYield 51.1%

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), 3,5-dimethyl-4-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-pyrrole-2-carbaldehyde (64.6 mg, 0.26 mmol) and piperidine (3 drops) in ethanol was stirred at room temperature under nitrogen for 2 days. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 65 mg (51%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.18 (br s, 1H, NH), 11.61 (br s, 1H, NH), 9.13 (br s, 1H), 8.26 (s, 1H), 7.70 (dd, J=2.4 & 6.9 Hz, 1H), 7.31-7.42 (m, 3H), 3.25 (m, 4H, 2×CH2), 2.63 (t, J=7.5 Hz, 2H, CH2), 2.35 (m, 2H, CH2), 2.31 (s, 3H, CH3), 2.12 (s, 3H, CH3), 1.76 (m, 4H, 2×CH2). MS 509 [M++1].

Workup

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

Sources & evidence

ORD record
ord-08b58e4e14dd44a3840177bd86b6619c
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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