N-Methyl-tert-butylamine → 5-[(7-{(2E)-4-[tert-Butyl(methyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)amino]-2,3-dichlorophenol

HRID 38612Notes

Reaction equation

HRID 38612 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][C:11]2[C:12]3[C:19]4[CH2:20][CH2:21][NH:22][CH2:23][C:18]=4[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][C:4]=1[OH:24].Br[CH2:26]/[CH:27]=[CH:28]/[C:29]([OH:31])=O.[C:32]([NH:36][CH3:37])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([N:36]([CH3:37])[CH2:26]/[CH:27]=[CH:28]/[C:29]([N:22]1[CH2:21][CH2:20][C:19]2[C:12]3[C:11]([NH:10][C:6]4[CH:7]=[C:8]([Cl:9])[C:3]([Cl:2])=[C:4]([OH:24])[CH:5]=4)=[N:16][CH:15]=[N:14][C:13]=3[S:17][C:18]=2[CH2:23]1)=[O:31])([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 3

HCID 84552N-Methyl-tert-butylamineHCID 64364114-Bromocrotonic acidHCID 668498872,3-Dichloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride

Product 1

HCID 581169365-[(7-{(2E)-4-[tert-Butyl(methyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)amino]-2,3-dichlorophenol

Procedure

The compound was synthesized in analogy to Example 147 from 2,3-dichloro-5-(5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride from Example 69A (85 mg, 0.21 mmol), (2E)-4-bromobut-2-enoic acid (52 mg, 0.32 mmol) and tert-butyl methylamine (29 mg, 0.34 mmol) to yield 18 mg (16%).

Workup

  1. customto yield 18 mg (16%)

Sources & evidence

ORD record
ord-f68b9af63e934509ad31c4d9f290cfe3
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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