(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride → N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[(2E)-4-(dimethylamino)but-2-enoyl]-6,7-dihydro-5H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38586Notes

Reaction equation

HRID 38586 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][NH:28][CH2:29][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl.[CH3:31][N:32]([CH3:39])[CH2:33]/[CH:34]=[CH:35]/[C:36](O)=[O:37]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][N:28]([C:36](=[O:37])/[CH:35]=[CH:34]/[CH2:33][N:32]([CH3:39])[CH3:31])[CH2:29][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

3

Reactant 2

HCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 58116925N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6,7-dihydro-5H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 58116918N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[(2E)-4-(dimethylamino)but-2-enoyl]-6,7-dihydro-5H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidin-4-amine

Procedure

In analogy to Example 89, the title compound was prepared from N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6,7-dihydro-5H-pyrrolo[3′,4′:4,5]thieno[2,3-d]pyrimidin-4-amine from Example 29A (46 mg, 0.11 mmol) and (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride from Example 1A (25 mg, 0.15 mmol) to yield 19 mg (33%).

Workup

  1. customto yield 19 mg (33%)

Sources & evidence

ORD record
ord-dec22e2b47e54d8a988cced6285957b0
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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