Acridan → n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-9,10-dihydroacridine

HRID 1827705Notes

Reaction equation

HRID 1827705 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:10]([CH2:11][N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][S:8][C:6]=2[N:7]=1.N[C:27]1N=C(N)C2C(C)=CSC=2N=1.C1C2CC3C(=CC=CC=3)NC=2C=CC=1>>[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:10]([CH2:11][N:12]3[C:19]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:27][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=4)=[CH:9][S:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 7106AcridanHCID 9906281n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamineHCID 12659534Thieno[2,3-d]pyrimidine-2,4-diamine, 5-methyl-

Product 1

HCID 22063030n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-9,10-dihydroacridine

Procedure

N-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-9,10-dihydroacridine (Formula I: Ar=2,4-diaminothieno[2,3-d]pyrimidi-5-yl; W=CH2; X=N; Z=CH2; m=n=0) is prepared similarly to N-[(2,4-diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-N,N-diphenylamine as disclosed in Example 11 above by using 2,4-diamino-5-methylthieno[2,3-d]pyrimidine (1.3 g, 7.4 mmol) in Step 1 and 9,10-dihydroacridine (134 mg, 0.8 mmol) in Step 3. The final product and its intermediates can b purified by chromatography.

Workup

  1. customThe final product and its intermediates can b purified by chromatography

Sources & evidence

ORD record
ord-2e692b5d60724436acb8f30162fc65f5
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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