Triethylamine → HCID 89579772, compound

HRID 928616Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([N:17]4[CH2:22][CH2:21][CH:20]([CH2:23][O:24][CH3:25])[CH2:19][CH2:18]4)=[N:14][C:13]([CH2:26][CH2:27]O)=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:29]([N:31](CC)[CH2:32][CH3:33])[CH3:30].CS(Cl)(=O)=O.N1CCCC1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([N:17]4[CH2:22][CH2:21][CH:20]([CH2:23][O:24][CH3:25])[CH2:19][CH2:18]4)=[N:14][C:13]([CH2:26][CH2:27][N:31]4[CH2:32][CH2:33][CH2:30][CH2:29]4)=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-[5-(4-Fluorophenyl)-4-[4-(methoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-2-yl]ethanol (20 mg, 0.05 mmol) was dissolved in THF (1 mL) to which was added triethylamine (0.021 mL, 0.15 mmol) and methanesulfonyl chloride (0.1 mmol). The reaction was stirred at 50° C. for 2 hrs then pyrrolidine (18 mg, 0.25 mmol) was added and the reaction stirred at 50° C. overnight. The reaction was partitioned between water and DCM. The organics wre concentrated in vacuo and the residue purified by preparative TLC, eluting with 7.5% 7M ammonia in methanol/DCM v/v to give 5-(4-fluorophenyl)-4-[4-(methoxymethyl)-1-piperidyl]-2-(2-pyrrolidin-1-ylethyl)thieno[2,3-d]pyrimidine (10 mg). LCMS RT=3.28 min. M+1=455.

Workup

stirringthe reaction stirred at 50° C. overnight
customThe reaction was partitioned between water and DCM
concentrationThe organics wre concentrated in vacuo
customthe residue purified by preparative TLC
washeluting with 7.5% 7M ammonia in methanol/DCM v/v

Sources & evidence

ORD record: ord-21dc622a8e36448f9cffe9a9402620fc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290511B2

Reaction notes

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