1-(Bromomethyl)-4-(1,1-dimethylethyl)benzene → 1-(4-tert-Butyl-benzyl)-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550725Notes

Reaction equation

HRID 550725 reaction equation
COC1C=C(OC)C=CC=1C[O:6][N:7]1[C:12](=[O:13])[C:11]2[S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[NH:9][C:8]1=[O:21].[C:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([C:32]1[CH:33]=[CH:34][C:35]([CH2:36][N:9]2[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[S:14][C:11]=3[C:12](=[O:13])[N:7]([OH:6])[C:8]2=[O:21])=[CH:38][CH:39]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 672009343-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 115237571-(4-tert-Butyl-benzyl)-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Procedure

Following general procedure B2 and D1, 3-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione (50 mg, 0.13 mmol) was alkylated with 4-tert-butyl benzyl bromide and subsequently deprotected to provide the title compound as a white solid (ret.=3.32 min., m/z=381.0): 1H NMR (d6-DMSO, 300 MHz) δ 1.20 (s, 9H); 5.64 (s, 2H); 7.17 (d, J=8 Hz, 1H); 7.25-7.60 (m, 5H); 7.95 (d, J=8 Hz, 1H); 8.08 (d, J=8 Hz, 1H).

Sources & evidence

ORD record
ord-4349daa775a7478e8c5430d9e92d6b67
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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