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

HRID 63915Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 3-(6-(4-chlorophenyl)-1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (See Compound 24, Step 3, 25 mg, 0.064 mmol) in EtOH (1 mL) was added NaBH4 (7.2 mg, 0.19 mmol). The reaction was stirred at 50° C. for 18 h, cooled to RT, quenched with diluted HCl (0.1N, 2 mL) then concentrated to a residue which was purified by Prep HPLC to give 6-(4-chlorophenyl)-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (10 mg, 43.0% yield) as a white solid. 1H NMR (CD3OD) δ: 7.46-7.45 (m, 4H), 4.10 (t, J=6.8 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H), 3.55 (s, 3H), 2.49 (s, 3H), 1.89-1.86 (m, 2H). LCMS: MH+ 365 and TR=2.742 min.

Workup

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

Sources & evidence

ORD record: ord-fc10d9c97fd14483a24c6218a42fac1e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447114B2

Reaction notes

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