3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-5-(5-methyl-3H-imidazol4-ylmethylene)-5,7-dihydro-pyrrolo [2,3-D]pyrimidin-6-one

HRID 1072142Notes

Reaction equation

HRID 1072142 reaction equation
Cl[C:2]1[C:3]2[C:10](=[CH:11][C:12]3[NH:13][CH:14]=[N:15][C:16]=3[CH3:17])[C:9](=[O:18])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:19][C:20]1[CH:21]=[C:22]([NH2:27])[CH:23]=[CH:24][C:25]=1[F:26]>>[Cl:19][C:20]1[CH:21]=[C:22]([NH:27][C:2]2[C:3]3[C:10](=[CH:11][C:12]4[NH:13][CH:14]=[N:15][C:16]=4[CH3:17])[C:9](=[O:18])[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:23]=[CH:24][C:25]=1[F:26]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 178433258HCID 178433258, compound2×

Product 1

HCID 1784332614-(3-Chloro-4-fluoro-phenylamino)-5-(5-methyl-3H-imidazol4-ylmethylene)-5,7-dihydro-pyrrolo [2,3-D]pyrimidin-6-oneYield 23%

Procedure

The title compound (23% yield) was prepared from 4-chloro-5-(5-methyl-3H-imidazol-4-ylmethylene)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one and 3-chloro-4-fluoro-phenylamine according to the procedure described for Example 12 without the conversion to the HCl salt. 1H NMR (360 MHz, DMSO-d6) δ 13.45 (br s, 1H, NH), 11.76 (br s, 1H, NH), 9.19 (s, 1H), 8.31 (s, 1H, H-vinyl), 7.92 (s, 1H), 7.73 (m, 1H), 7.45 (m, 2H), 7.36 (m, 1H), 2.33 (s, 3H7CH3). MS 371.4 [M++1].

Sources & evidence

ORD record
ord-11856cba80544a589e8a10f14b2887be
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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