Sodium borohydride → 5-(4-chlorobenzyl)-6-(4-chlorophenyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63914Notes

Reaction equation

[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][C:19](OC)=[O:20])[C:12](=[O:23])[N:11]([CH3:24])[C:10]=3[S:9][C:8]=2[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:23])[N:11]([CH3:24])[C:10]=3[S:9][C:8]=2[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 3-(5-(4-chlorobenzyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (13 mg, 0.0258 mmol) in EtOH (1 mL) was added NaBH4 (2.9 mg, 0.0775 mmol). The reaction was stirred at 50° C. for 18 h, cooled to RT, quenched with aq. HCl (0.1 N, 2 mL) then concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(4-chlorophenyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (8.6 mg, 70.1% yield) as a white solid. 1H NMR (CD3OD) δ: 7.43 (d, J=8.4 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H), 7.19 (d, J=8.4 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H) 4.32 (S, 2H), 4.05 (t, J=7.2 Hz, 2H), 3.55-3.58 (m, 5H), 1.84-1.82 (m, 2H). LCMS: MH+ 475 and TR=3.131 min.

Workup

temperaturecooled to RT
customquenched with aq. HCl (0.1 N, 2 mL)
concentrationthen concentrated to a residue which
customwas purified by Prep HPLC

Sources & evidence

ORD record: ord-fff31325634c42d482cab2c848f95691
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447114B2

Reaction notes

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